Herbicidal compositions containing benzoylpyrazole compounds

ABSTRACT

[OBJECT] 
     To provide a novel pesticide. 
     [MEANS OF ACCOMPLISHING THE OBJECT] 
     The present invention provides a herbicidal composition which comprises as active ingredients (a) a herbicidal benzoylpyrazole compound represented by the formula (I) or its salt: 
     
       
         
         
             
             
         
       
     
     wherein R 1  is alkyl or cycloalkyl, R 2  is a hydrogen atom or alkyl, R 3  is alkyl, R 4  is alkyl, haloalkyl or the like, R 5  is a hydrogen atom, alkyl or the like, R 6  is haloalkyl, halogen or the like, and A is alkylene substituted by alkyl, and (b) other herbicidal compound.

CROSS REFERENCE TO RELATED APPLICATION

This application is a continuation application of U.S. patent application Ser. No. 13/133,993, filed on Jun. 10, 2011, which was a National Stage entry under 35 USC 371 of PCT/JP2009/071004, filed on Oct. 12, 2009, and claims priority to Japanese Patent Application No. 2008-316203, filed on Dec. 11, 2008.

TECHNICAL FIELD

The present invention relates to herbicidal compositions containing as active ingredients (a) a herbicidal benzoylpyrazole compound or its salt and (b) other herbicidal compound.

BACKGROUND ART

In Patent Documents 1 and 2, it is disclosed that certain pyrazole compounds are useful as herbicides, and some other herbicides which can be used as mixed with such compounds, are exemplified. Patent Document 3 discloses mixed use of certain pyrazole compounds with other herbicides. However, these documents do not specifically disclose a herbicidal composition comprising as active ingredients a herbicidal benzoylpyrazole compound represented by the following formula (I) and other herbicidal compound.

-   [PATENT DOCUMENT 1] EP352543A -   [PATENT DOCUMENT 2] WO2008/065907 -   [PATENT DOCUMENT 3] WO2008/093840

DISCLOSURE OF THE INVENTION Object to be Accomplished by the Invention

At present, many herbicidal compositions have been developed and used, but there are a variety of types of weeds to be controlled, and their development lasts for a long period of time. Thus, a high activity and long lasting herbicidal composition having a wider herbicidal spectrum has been desired. Further, in recent years, a technique to reduce the dose of the active ingredient has been desired so as to reduce the environmental load to a place where the herbicide is applied or a periphery thereof.

Means to Accomplish the Object

The present inventors have conducted extensive studies to accomplish the above object and as a result, found a highly useful herbicidal composition.

That is, the present invention relates to a herbicidal composition which comprises as active ingredients (a) a herbicidal benzoylpyrazole compound represented by the formula (I) or its salt (hereinafter referred to as compound Q):

wherein R¹ is alkyl or cycloalkyl, R² is a hydrogen atom or alkyl, R³ is alkyl, R⁴ is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R⁵ is a hydrogen atom; alkyl; alkenyl; alkynyl; halogen; cyano; cyanoalkyl; cyanoalkenyl; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷; thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; alkoxyhaloalkoxy; halo alkoxyhaloalkoxy; alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio; halo alkoxyalkylthio; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthiohaloalkylthio; haloalkylthiohaloalkylthio; alkylthioalkoxy; alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl; alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy; heterocyclylalkoxy; heterocyclylalkoxyalkyl; heterocyclyloxyalkyl; cycloalkyloxy; —OC(O)SR⁷; —OC(O)OR⁷; —C(O)OR⁷; —C(O)SR-7; —C(S)OR⁷; —C(S)SR⁷; or aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR⁷ and —C(O)SR⁷, R⁶ is haloalkyl; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, A is alkylene substituted by at least one alkyl, R⁷ is alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl which may be substituted by R⁸, and each of R⁸ which is independent of one another, is halogen; alkyl; or alkoxy, and (b) other herbicidal compound. Further, the present invention relates to a method for controlling undesired plants, which comprises applying a herbicidally effective amount of the above herbicidal composition to the undesired plants or to a place where they grow. Further, the present invention relates to a method for controlling undesired plants, which comprises applying a herbicidally effective amount of the compound Q and a herbicidally effective amount of other herbicidal compound to the undesired plants or to a place where they grow.

Effects of the Invention

The herbicidal composition of the present invention, i.e. the herbicidal composition comprising as active ingredients the compound Q and other herbicidal compound, is capable of controlling a wide range of undesired plants emerging in agricultural fields or non-agricultural fields. It surprisingly presents a synergistic herbicidal effect i.e. a herbicidal effect higher than the mere addition of the respective herbicidal effects of the active ingredients. Such a herbicidal composition of the present invention can be applied at a low dose as compared with a case where the respective active ingredients are applied individually. Thus, it is effective to reduce the environmental load on a place where the composition is applied or a periphery thereof. Further, the herbicidal spectrum will be enlarged, and further the herbicidal effects will last over a long period of time.

When the herbicidal activity in a case where two active ingredients are combined, is larger than the simple sum of the respective herbicidal activities of the two active ingredients (the expected activity), it is called a synergistic effect. The activity expected by the combination of two active ingredients can be calculated as follows (Colby S. R., “Weed”, vol. 15, p. 20-22, 1967). E=α+β−(α×β÷100) where

α: growth inhibition rate when treated with x (g/ha) of herbicide X,

β: growth inhibition rate when treated with y (g/ha) of herbicide Y,

E: growth inhibition rate expected when treated with x (g/ha) of herbicide X and y (g/ha) of herbicide Y.

That is, when the actual growth inhibition rate (measured value) is larger than the growth inhibition rate by the above calculation (calculated value), the activity by the combination can be regarded as showing a synergistic effect. The herbicidal composition of the present invention shows a synergistic effect when calculated by the above formula.

BEST MODE(S) FOR CARRYING OUT THE INVENTION

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ and A in the formula (I) will be described in detail below.

The alkyl or alkyl moiety in each of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ and A may be linear or branched, and specific examples thereof include C₁₋₉ alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, isohexyl, n-heptyl, n-octyl and n-nonyl.

Examples of the cycloalkyl or cycloalkyl moiety in each of R¹ and R⁵ include C₃₋₆ cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The alkenyl or alkenyl moiety in each of R⁵ and R⁷ may be linear or branched, and specific examples thereof include C₂₋₉ alkenyl such as vinyl, 1-propenyl, 2-propenyl, isopropenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 2-pentenyl, 4-pentenyl, 2-hexenyl, 4-hexenyl, 2-heptenyl, 4-heptenyl, 2-octenyl, 6-octenyl and 2-nonenyl.

The alkynyl or alkynyl moiety in each of R⁵ and R⁷ may be linear or branched, and specific examples thereof include C₂₋₉ alkynyl such as ethynyl, propargyl, 1-propynyl, 1-pentynyl, 3-pentynyl, 1-heptynyl and 1-nonynyl.

Examples of halogen or halogen as the substituent in each of R⁴, R⁵, R⁶, R⁷ and R⁸ include atoms of fluorine, chlorine, bromine and iodine.

The number of halogens as substituents in each of R⁴, R⁵, R⁶ and R⁷ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution of such halogens may be any positions.

The number of alkoxy or alkoxy moieties as substituents in each of R⁵ and R⁷ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution may be any positions.

Examples of the aryl moiety as the substituent in R⁷ include phenyl and naphthyl. The number of aryl or aryl moieties as substituents may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution may be any positions.

The number of R⁸ as substituents which substitute the arylalkyl in R⁷ may be 1 or more, and if more, they may be the same or different. Further, the positions for substitution of such substituents may be any positions.

The alkoxyalkoxy in R⁵ is meant for an alkoxy group having the same or different alkoxy moiety bonded thereto. The position for substitution of the alkoxy moiety which substitutes the alkoxy group may be any position. The same applies to haloalkoxyalkoxy, alkoxyhaloalkoxy, alkoxyalkoxyalkyl, alkylthioalkylthio, alkylsulfonylalkyl, alkoxycarbonylalkyl, etc.

The heterocyclyl moiety in R⁵ may, for example, be a saturated or unsaturated 5-membered or 6-membered ring containing 1 to 4 one or more types of hetero atoms optionally selected from O, S and N, and specific examples thereof include oxolanyl, 1,3-dioxolanyl, tetrahydrofuranyl and tetrahydro-2H-pyranyl. Further, the number of heterocyclyl moieties as substituents may be 1 or more, and if more, they may be the same or different. The positions for substitution of the heterocyclyl moieties may be any positions.

The alkylene moiety in A may, for example, be C₁₋₉ alkylene such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene or nonamethylene.

The salt of the herbicidal benzoylpyrazole compound of the formula (I) includes all kinds of salts so long as they are agriculturally acceptable. Examples thereof include alkali metal salts such as a sodium salt and a potassium salt; alkaline earth metal salts such as a magnesium salt and a calcium salt; amine salts such as a dimethylamine salt and a triethylamine salt; inorganic acid salts such as a hydrochloride, a perchlorate, a sulfate and a nitrate; and organic acid salts such as an acetate and a methanesulfonate.

In a case where various structural isomers such as optical isomers, geometric isomers, etc. exist as the compound Q, they are, of course, all included.

Other herbicidal compound in the present invention includes, for example, the following compounds (by common names including ones under application for approval by ISO, or test codes), and one or more may suitably be selected. Even when not specifically mentioned here, in a case where such compounds have salts, alkyl esters, hydrates, different crystal forms, various structural isomers, etc., they are, of course, all included.

(1) Those which are believed to exhibit herbicidal effects by disturbing hormone activities of plants, such as a phenoxy type such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4-D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop-potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, naproanilide or clomeprop; an aromatic carboxylic acid type such as 2,3,6-TBA, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, dichlobenil, picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium, picloram-trolamine, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium or aminopyralid; and others such as naptalam, naptalam-sodium, benazolin, benazolin-ethyl, quinclorac, quinmerac, diflufenzopyr, diflufenzopyr-sodium, fluoroxypyr, fluoroxypyr-2-butoxy-1-methylethyl, fluoroxypyr-meptyl, chlorflurenol or chlorflurenol-methyl.

(2) Those which are believed to exhibit herbicidal effects by inhibiting photosynthesis of plants, such as a urea type such as chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, karbutilate, methabenzthiazuron, metoxuron, monolinuron, neburon, siduron, terbumeton or trietazine; a triazine type such as simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, terbuthylazine, cyanazine, ametryn, cybutryne, triaziflam, terbutryn, propazine, metamitron or prometon; a uracil type such as bromacil, bromacyl-lithium, lenacil or terbacil; an anilide type such as propanil or cypromid; a carbamate type such as swep, desmedipham or phenmedipham; a hydroxybenzonitrile type such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynil-octanoate, ioxynil-potassium or ioxynil-sodium; and others such as pyridate, bentazone, bentazone-sodium, amicarbazone, methazole or pentanochlor.

(3) Quaternary ammonium salt type such as paraquat or diquat, which is believed to be converted to free radicals by itself to form active oxygen in the plant body and shows rapid herbicidal efficacy.

(4) Those which are believed to exhibit herbicidal effects by inhibiting chlorophyll biosynthesis of plants and abnormally accumulating a photosensitizing peroxide substance in the plant body, such as a diphenylether type such as nitrofen, chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesafen-sodium, oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl (HC-252), fluoroglycofen-ethyl or fluoroglycofen; a cyclic imide type such as chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl or fluthiacet-methyl; and others such as oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin, isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil, flupoxam, fluazolate, profluazol, pyraclonil, flufenpyr-ethyl or bencarbazone.

(5) Those which are believed to exhibit herbicidal effects characterized by bleaching activities by inhibiting chromogenesis of plants such as carotenoids, such as a pyridazinone type such as norflurazon, chloridazon or metfiurazon; a pyrazole type such as pyrazolynate, pyrazoxyfen, benzofenap, topramezone or pyrasulfotole; and others such as amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione, mesotrione, tembotrione, tefuryltrione (AVH-301), isoxaflutole, difenzoquat, difenzoquat-metilsulfate, isoxachlortole, benzobicyclon, picolinafen or beflubutamid.

(6) Those which exhibit strong herbicidal effects specifically to gramineous plants, such as an aryloxyphenoxypropionic acid type such as diclofop-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P, fluazifop-P-butyl, haloxyfop-methyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, haloxyfop-P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metamifop, clodinafop-propargyl, clodinafop or propaquizafop; a cyclohexanedione type such as alloxydim-sodium, alloxydim, clethodim, sethoxydim, tralkoxydim, butroxydim, tepraloxydim, profoxydim or cycloxydim; and others such as flamprop-M-methyl, flamprop-M or flamprop-M isopropyl.

(7) Those which are believed to exhibit herbicidal effects by inhibiting an amino acid biosynthesis of plants, such as a sulfonylurea type such as chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, chlorsulfuron, metsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl, pyrazosulfuron, azimsulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, cyclosulfamuron, prosulfuron, flupyrsulfuron-methyl-sodium, flupyrsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl, halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, oxasulfuron, ethametsulfuron, ethametsulfuron-methyl, iodosulfuron, iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron, tritosulfuron, foramsulfuron, trifloxysulfuron, trifloxysulfuron-sodium, mesosulfuron-methyl, mesosulfuron, orthosulfamuron, flucetosulfuron, amidosulfuron, propyrisulfuron (TH-547) or a compound disclosed in the claim of WO2005092104; a triazolopyrimidinesulfonamide type such as flumetsulam, metosulam, diclosulam, cloransulam-methyl, florasulam, penoxsulam or pyroxsulam; an imidazolinone type such as imazapyr, imazapyr-isopropylammonium, imazethapyr, imazethapyr-ammonium, imazaquin, imazaquin-ammonium, imazamox, imazamox-ammonium, imazamethabenz, imazamethabenz-methyl or imazapic; a pyrimidinylsalicylic acid type such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid or pyrimisulfan; a sulfonylaminocarbonyltriazolinone type such as flucarbazone, flucarbazone-sodium, propoxycarbazone-sodium or propoxycarbazone; and others such as glyphosate, glyphosate sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate-isopropylammonium, glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, bilanafos, bilanafos-sodium or cinmethylin.

(8) Those which are believed to exhibit herbicidal effects by inhibiting cell mitoses of plants, such as a dinitroaniline type such as trifluralin, oryzalin, nitralin, pendimethalin, ethalfluralin, benfluralin, prodiamine, butralin or dinitramine; an amide type such as bensulide, napropamide, propyzamide or pronamide; an organic phosphorus type such as amiprofos-methyl, butamifos, anilofos or piperophos; a phenyl carbamate type such as propham, chiorpropham, barban or carbetamide; a cumylamine type such as daimuron, cumyluron, bromobutide or methyldymron; and others such as asulam, asulam-sodium, dithiopyr, thiazopyr, chlorthal-dimethyl, chlorthal or diphenamid.

(9) Those which are believed to exhibit herbicidal effects by inhibiting protein biosynthesis or lipid biosynthesis of plants, such as a chloroacetamide type such as alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, thenylchlor, pethoxamid, acetochlor, propachlor, dimethenamid, dimethenamid-P, propisochloror dimethachlor; a thiocarbamate type such as molinate, dimepiperate, pyributicarb, EPTC, butylate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, thiobencarb, diallate, tri-allate or orbencarb; and others such as etobenzanid, mefenacet, flufenacet, tridiphane, cafenstrole, fentrazamide, oxaziclomefone, indanofan, benfuresate, pyroxasulfone, dalapon, dalapon-sodium, TCA-sodium or trichloroacetic acid.

(10) MSMA, DSMA, CMA, endothall, endothall-dipotassium, endothall-sodium, endothall-mono(N,N-dimethylalkylammonium), ethofumesate, sodium chlorate, pelargonic acid (nonanoic acid), fosamine, fosamine-ammonium, pinoxaden, ipfencarbazone (HOK-201), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid, dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC, ferrous sulfate, flupropanate, flupropanate-sodium, isoxaben, mefluidide, mefluidide-diolamine, metam, metam-ammonium, metam-potassium, metam-sodium, methyl isothiocyanate, pentachlorophenol, sodium pentachlorophenoxide, pentachlorophenol laurate, quinoclamine, sulfuric acid, urea sulfate, etc.

(11) Those which are believed to exhibit herbicidal effects by being parasitic on plants, such as Xanthomonas campestris, Epicoccosirus nematosorus, Epicoccosirus nematosperus, Exserohilum monoseras or Drechsrela monoceras.

The herbicidal composition of the present invention has excellent herbicidal effects. The application range extends to agricultural fields such as paddy fields, crop plant fields, orchards and mulberry fields and non-agricultural fields such as forest land, farm roads, play grounds and factory sites. The application method may suitably be selected from soil application, foliar application, water application, etc.

The herbicidal composition of the present invention are capable of controlling a wide range of undesired weeds, such as gramineae such as bamyardgrass (Echinochloa crus-galli L., Echinochloa oryzicola vasing.), crabgrass (Digitaria sanguinalis L., Digitaria ischaemum Muhl., Digitaria adscendens Henr., Digitaria microbachne Henr., Digitaria horizontalis Willd.), green foxtail (Setaria viridis L.), giant foxtail (Setaria faberi Herrm.), yellow foxtail (Setaria lutescens Hubb.), goosegrass (Eleusine indica L.), wild oat (Avena fatua L.), johnsongrass (Sorghum halepense L.), quackgrass (Agropyron repens L.), alexandergrass (Brachiaria plantaginea), guineagrass (Panicum maximum Jacq.), paragrass (Panicum purpurascens), sprangletop (Leptochloa chinensis), red sprangletop (Leptochloa panicea), annual bluegrass (Poe annua L.), black grass (Alopecurus mvosuroides Huds.), cholorado bluestem (Agropvron tsukushiense (Honda) Ohwi), broadleaf signalgrass (Brachiaria platvphylla Nash), southern sandbur (Cenchrus echinatus L.), italian ryegrass (Lolium multiflorum Lam.), and bermudagrass (Cynodon dactylon Pers.); cyperaceae such as rice flatsedge (Cyperus iria L.), purple nutsedge (Cyperus rotundus L.), yellow nutsedge (Cvperus esculentus L.), Japanese bulrush (Scirpus juncoides), flatsedge (Cyperus serotinus), small-flower umbrellaplant (Cyperus difformis), slender spikerush (Eleocharis acicularis), and water chestnut (Eleocharis kuroquwai); alismataceae such as Japanese ribbon waparo (Sagittaria pygmaea), arrow-head (Sagittaria trifolia), and narrowleaf waterplantain (Alisma canaliculatum); pontederiaceae such as monochoria (Monochoria vaginalis), and monochoria species (Monochoria korsakowii); scrophulariaceae such as false pimpernel (Lindemia pvxidaria), and abunome (Dopatrium junceum); lythraceae such as toothcup (Rotala india), and red stem (Ammannia multiflora); elatinaceae such as long stem waterwort (Elatine triandra SCHK.); malvaceae such as velvetleaf (Abutilon theophrasti MEDIC.), and prickly sida (Side spinosa L.); compositae such as common cocklebur (Xanthium strumarium L.), common ragweed (Ambrosia elatior L.), thistle (Breea setosa (BIEB.) KITAM.), hairy galinsoga (Galinsoga ciliata Blake), wild chamomile (Matricaria chamomilla L.); solanaceae such as black nightshade (Solanum nigrum L.), and jimsonweed (Datura stramonium); amaranthaceae such as slender amaranth (Amaranthus viridis L.), and redroot pigweed (Amaranthus retroflexus L.); polygonaceeae such as pale smartweed (Polygonum lapathifolium L.), ladysthumb (Polygonum persicaria L.), wild buckwheat (Polygonum convolvulus L.), and knotweed (Polygonum aviculare L.); cruciferae such as flexuous bittercress (Cardamine flexuosa WITH.), shepherd's-purse (Capsella bursa-pastoris Medik.), and indian mustard (Brassica juncea Czern.); convolvulaceae such as tall morningglory (Ipomoea purpurea L.), field bindweed (Calystegia arvensis L.), and ivyleaf morningglory (Ipomoea hederacea Jacq.); Chenopodiaceae such as common lambsquarters (Chenopodium album L.), and mexican burningbush (Kochia scoparia Schrad.); Portulacaceae such as common purslane (Portulaca oleracea L.); leguminosae such as sicklepod (Cassia obtusifolia L.); caryophyllaceae such as common chickweed (Stellaria media L.); labiatae such as henbit (Lamium amplexicaule L.); rubiaceae such as catchweed (Galium spurium L.); euphorbiaceae such as threeseeded copperleaf (Acalvpha australis L.); and Commelinaceae such as common dayflower (Commelina communis L.).

Therefore, they can be effectively used for selectively controlling noxious weeds in cultivation of useful crops such as corn (Zea mays L.), soybean (Glycine max Merr.), cotton (Gossypium spp.), wheat (Triticum spp.), rice (Oryza sativa L.), barley (Hordeum vulgare L.), rye (Secale cereale L.), oat (Avena sativa L.), sorgo (Sorghum bicolor Moench), rape (Brassica napus L.), sunflower (Helianthus annuus L.), sugar beet (Beta vulgaris L.), sugar cane (Saccharum officinarum L.), japanese lawngrass (Zoysia japonica stend), peanut (Arachis hypogaea L.), flax (Linum usitatissimum L.), tobacco (Nicotiana tabacum L.), and coffee (Coffea spp.). Particularly, the herbicidal composition of the present invention are effectively used for selectively controlling noxious weeds in cultivation of corn, soybean, cotton, wheat, rice, rape, sunflower, sugar beet, sugar cane, japanese lawngrass, peanut, flax, tobacco, coffee, and the like, and among these, especially corn, wheat, rice, and the like. And the herbicidal composition of the present invention can be effectively used for nonselectively controlling noxious weeds.

The herbicidal composition of the present invention is effectively used to selectively control noxious weeds in cultivation of various transformed plants. Examples of the transformed plants include pest-resistant transformed plants, phytopathogen-resistant transformed plants, transformed plants regarding plant components, transformed plants resistant to the compound Q, and transformed plants resistant to other herbicidal compound.

Examples of a site where the herbicidal composition of the present invention is applied include a corn field, a wheat, a barley or a rye field, a rice field and a non-agricultural field. One or more of other herbicidal compounds may suitably be selected and used depending upon the application site, and examples thereof include the following.

In a case where undesired plants are selectively controlled in a corn field, for example, said other herbicidal compound is at least one compound selected from the group consisting of a phenoxy compound, an aromatic carboxylic acid compound, a urea compound, a triazine compound, a hydroxybenzonitrile compound, a diphenylether compound, a cyclic imide compound, a pyrazole compound, a sulfonylurea compound, a triazolopyrimidinesulfonamide compound, an imidazolinone compound, a dinitroaniline compound, a chloroacetamide compound, a thiocarbamate compound, benazolin, benazolin-ethyl, diflufenzopyr, diflufenzopyr-sodium, fluoroxypyr, fluoroxypyr-2-butoxy-1-methylethyl, fluoroxypyr-meptyl, pyridate, bentazone, bentazone-sodium, amicarbazone, carfentrazone-ethyl, saflufenacil, flufenpyr-ethyl, bencarbazone, fluridone, clomazone, sulcotrione, mesotrione, tembotrione, isoxaflutole, difenzoquat, difenzoquat-metilsulfate, isoxachlortole, glyphosate, glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate-isopropylammonium, glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, flufenacet, tridiphane, benfuresate, pyroxasulfone, dalapon, dalapon-sodium, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate and DNOC.

More preferably, a phenoxy compound such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonimum, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4-D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, dichiorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop-potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl or mecoprop-P-potassium; an aromatic carboxylic acid compound such as dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, clopyralid, clopyralid-olamine, clopyralid-potassium or clopyralid-triisopropanolammonium; a urea compound such as diuron, linuron, metobenzuron, methabenzthiazuron or monolinuron; a triazine compound such as simazine, atrazine, metribuzin, terbuthylazine, cyanazine, ametryn, terbutryn or propazine; a hydroxybenzonitrile compound such as bromoxynil, bromoxynil-octanoate or bromoxynil-heptanoate; a diphenylether compound such as bifenox, oxyfluorfen or aclonifen; a cyclic imide compound such as flumiclorac-pentyl, cinidon-ethyl or fluthiacet-methyl; a pyrazole compound such as topramezone; a sulfonylurea compound such as primisulfuron-methyl, primisulfuron, rimsulfuron, nicosulfuron, prosulfuron, flupyrsulfuron-methyl-sodium, flupyrsulfuron, halosulfuron-methyl, halosulfuron, thifensulfuron-methyl, thifensulfuron, iodosulfuron, iodosulfuron-methyl-sodium, tritosulfuron or foramsulfuron; a triazolopyrimidinesulfonamide compound such as flumetsulam, metosulam or florasulam: an imidazolinone compound such as imazamox or imazamox-ammonium; a dinitroaniline compound such as pendimethalin, ethalfiuralin or prodiamine; a chloroacetamide compound such as alachlor, metazachior, metolachlor, S-metolachlor, pethoxamid, acetochlor, propachior, dimethenamid or dimethenamid-P; a thiocarbamate compound such as EPTC, butyrate, triallate or orbencarb; benazolin; benazolin-ethyl; diflufenzopyr, diflufenzopyr-sodium; fluoroxypyr; fluoroxypyr-2-butoxy-1-methylethyl; fluoroxypyr-meptyl; pyridate; bentazone; bentazone-sodium; amicarbazone; carfentrazone-ethyl; saflufenacil; flufenpyr-ethyl; bencarbazone; fluridone; clomazone; sulcotrione; mesotrione; tembotrione; isoxaflutole; difenzoquat; difenzoquat-metilsulfate; isoxachlortosinate-ammonium; flufenacet; tridiphane; benfuresate; pyroxasulfone; dalapon, dalapon-sodium; dinoterb; dinoterb-ammonium; dinoterb-diolamine, dinoterb-acetate; or DNOC may, for example, be used.

In a case where undesired plants are selectively controlled in a wheat, a barley or a rye field, for example, said other herbicidal compound is at least one compound selected from the group consisting of a phenoxy compound, an aromatic carboxylic acid compound, a urea compound, a triazine compound, an anilide compound, a hydroxybenzonitrile compound, a diphenylether compound, a cyclic imide compound, a pyrazole compound, an aryloxyphenoxypropionic acid compound, a cyclohexanedione compound, a sulfonylurea compound, a triazolopyrimidinesulfonamide compound, an imidazolinone compound, a pyrimidinylsalicylic acid compound, a sulfonylaminocarbonyltriazolinone compound, a dinitroaniline compound, a phenyl carbamate compound, a chloroacetamide compound, a thiocarbamate compound, benazolin, benazolin-ethyl, quinclorac, quinmerac, fluoroxypyr, fluoroxypyr-2-butoxy-1-methylethyl, fluoroxypyr pyridate, bentazone, bentazone-sodium, carfentrazone-ethyl, thidiazimin, pyraflufen-ethyl, saflufenacil, flupoxam, fluazolate, bencarbazone, flurtamone, diflufenican, sulcotrione, difenzoquat, difenzoquat-metilsulfate, picolinafen, beflubutamid, flamprop-M-methyl, flamprop-M, flamprop-M

isopropyl, flufenacet, indanofan, pinoxaden, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC and isoxaben.

More preferably, a phenoxy compound such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonimum, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4-D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop-potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl or mecoprop-P-potassium; an aromatic carboxylic acid compound such as 2,3,6-TBA, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, dichlobenil, picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium, picloram-trolamine, clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium or aminopyralid; a urea compound such as chlorotoluron, diuron, linuron, isoproturon, dimefuron, methabenzthiazuron, metoxuron or neburon; a triazine compound such as prometryn, metribuzin, cyanazine or terbutryn; an anilide compound such as propanil or cypromid, a hydroxybenzonitrile compound such as bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynil-octanoate, ioxynil-potassium or ioxynil-sodium; a diphenylether compound such as bifenox, oxyfluorfen, aclonifen, ethoxyfen-ethyl, fluoroglycofen-ethyl or fluoroglycofen; a cyclic imide compound such as cinidon-ethyl, a pyrazole compound such as pyrasulfotole; an aryloxyphenoxypropionic acid compound such as diclofop-methyl, diclofop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, clodinafop-propargyl or clodinafop; a cyclohexanedione compound such as tralkoxydim or butroxydim; a sulfonylurea compound such as chiorsulfuron, metsulfuron-methyl, metsulfuron, cyclosulfamuron, prosulfuron, flupyrsulfuron-methyl-sodium, flupyrsulfuron, halosulfuron-methyl, halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, iodosulfuron-methyl-sodium, iodosulfuron, sulfosulfuron, triasulfuron, tribenuron methyl, tribenuron, tritosulfuron, mesosulfuron-methyl, mesosulfuron, flucetosulfuron or amidosulfuron; a triazolopyrimidinesulfonamide compound such as flumetsulam, metosulam or florasulam; an imidazolinone compound such as imazamox, imazamox-ammonium, imazamethabenz or imazamethabenz-methyl; a pyrimidinylsalicylic acid compound such as pyribenzoxim; a sulfonylaminocarbonyltriazolinone compound such as flucarbazone, flucarbazone sodium, propoxycarbazone or propoxycarbazone-sodium; a dinitroaniline compound such as pendimethalin or butralin; a phenyl carbamate compound such as barban; a chloroacetamide compound such as butachlor; a thiocarbamate compound such as prosulfocarb, triallate or orbencarb; benazolin, benazolin-ethyl, quinclorac, quinmerac, fluoroxypyr, fluoroxypyr-2-butoxy-1-methylethyl, fluoroxypyr-meptyl, pyridate, bentazone, bentazone-sodium, carfentrazone-ethyl, thidiazimin, pyraflufen-ethyl, saflufenacil, flupoxam, fluazolate, bencarbazone, flurtamone, diflufenican, sulcotrione, difenzoquat, difenzoquat-metilsulfate, picolinafen, beflubutamid, flamprop-M-methyl, flamprop-M, flamprop-M-isopropyl, flufenacet, indanofan, pinoxaden, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC; or isoxaben may, for example, be used.

In a case where undesired plants are selectively controlled in a rice field, for example, said other herbicidal compound is at least one compound selected from the group consisting of a phenoxy compound, an aromatic carboxylic acid compound, a urea compound, a triazine compound, an anilide compound, a carbamate compound, a diphenylether compound, a pyrazole compound, an aryloxyphenoxypropionic acid compound, a cyclohexanedione compound, a sulfonylurea compound, a triazolopyrimidinesulfonamide compound, a pyrimidinylsalicylic acid compound, a dinitroaniline compound, an organic phosphorus compound, a cumylamine compound, a chloroacetamide compound, a thiocarbamate compound, those which are believed to exhibit herbicidal effects by being parasitic on plants, quinclorac, quinmerac, pyridate, bentazone, bentazone-sodium, oxadiargyl, oxadiazon, carfentrazone-ethyl, pentoxazone, pyraclonil, fluridone, diflufenican, methoxyphenone, clomazone, mesotrione, tefuryltrione, benzobicyclon, cinmethylin, dithiopyr, etobenzanide, mefenacet, flufenacet, cafenstrole, fentrazamide, oxaziclomefone, indanofan, benfuresate, TCA-sodium, trichloroacetic acid, ipfencarbazone and quinoclamine.

More preferably, a phenoxy compound such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonimum, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4-D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichlorprop-potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, naproanilide or clomeprop; an aromatic carboxylic acid compound such as picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium, picloram-trolamine, triclopyr, triclopyr-butotyl or triclopyr-triethylammonium; a urea compound such as linuron; a triazine compound such simetryn, prometryn, dimethametryn or triaziflam; an anilide compound such as propanil; a carbamate compound such as swep; a diphenylether compound such as nitrofen, chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, oxyfluorfen, fluoroglycofen-ethyl or fluoroglycofen; a pyrazole compound such as pyrazolynate, pyrazoxyfen or benzofenap; an aryloxyphenoxypropionic acid compound such as cyhalofop-butyl, metamifop-propyl or metamifop; a cyclohexanedione compound such as profoxydim; a sulfonylurea compound such as bensulfuron-methyl, bensulfuron, metsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl, pyrazosulfuron, azimsulfuron, imazosulfuron, cyclosulfamuron, halosulfuron-methyl, halosulfuron, ethoxysulfuron, orthosulfamuron, flucetosulfuron or propyrisulfuron; a triazolopyrimidinesulfonamide compound such as penoxsulam; a pyrimidinylsalicylic acid compound such as bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid or pyrimisulfan; a dinitroaniline compound such as oryzalin, pendimethalin or butralin; an organic phosphorus compound such as butamifos, anilofos or piperophos; a cumylamine compound such as daimuron, cumyluron or bromobutide; a chloroacetamide compound such as butachlor, pretilachloror thenylchlor; a thiocarbamate compound such as molinate, dimepiperate, pyributicarb, esprocarb or thiobencarb; quinclorac; quinmerac; pyridate; bentazone; bentazone-sodium; oxadiargyl; oxadiazon; carfentrazone-ethyl; pentoxazone; pyraclonil, fluridone; diflufenican; methoxyphenone; clomazone; mesotrione; tefuryltrione; benzobicyclon; cinmethylin; dithiopyr; etobenzanide; mefenacet; flufenacet; cafenstrole; fentrazamide; oxaziclomefone; indanofan; benfuresate; TCA-sodium; trichloroacetic acid; ipfencarbazone; or quinoclamine may, for example, be used.

In a case where undesired plants are nonselectively controlled, for example, said other herbicidal compound is at least one compound selected from the group consisting of a phenoxy compound, an aromatic carboxylic acid compound, a urea compound, a triazine compound, a uracil compound, a hydroxybenzonitrile compound, a quaternary ammonium salt compound, a sulfonylurea compound, an imidazolinone compound, a pyrimidinylsalicylic acid compound, a dinitroaniline compound, benazolin, benazolin-ethyl, diflufenzopyr, diflufenzopyr-sodium, chlorflurenol, chlorflurenol-methyl, pentanochior, butafenacil, glyphosate, glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate-isopropylammonium, glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, bilanafos, bilanafos-sodium, asulam, asulam-sodium, dalapon, dalapon-sodium, TCA-sodium, trichloroacetic acid, CMA, fosamine, fosamine-ammonium, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, methylarsonic acid, dimethylarsinic acid, sodium dimethylarsinate, flupropanate, flupropanate-sodium, isoxaben, mefluidide, mefluidide-diolamine, pentachlorophenol, pentachlorophenol-sodium and pentachlorophenol-laurate.

More preferably, a phenoxy compound such as 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonimum, 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl, 2,4-D-isobutyl, 2,4-D

isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-sodium, 2,4-D-isopropanolammonium, 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, dichiorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-isoctyl, dichiorprop-potassium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-potassium, dichlorprop-P-sodium, MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethylhexyl, MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPB, MCPB-ethyl, MCPB-sodium, mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl or mecoprop-P-potassium; an aromatic carboxylic acid compound such as 2,3,6-TBA, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, dichlobenil, picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium, picloram-trolamine, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium or aminopyralid; a urea compound such as diuron, tebuthiuron, isouron, karbutilate, monolinuron or neburon; a triazine compound such as atrazine, hexazinone, terbuthylazine, cyanazine, ametryn, propazine or prometon; a uracil compound such as bromacil or bromacyl-lithium; a hydroxybenzonitrile compound such as bromoxynil, bromoxynil-octanoate or bromoxynil-heptanoate; a quaternary ammonium salt compound such as paraquat or diquat; a sulfonylurea compound such as sulfometuron-methyl, sulfometuron, chlorsulfuron, flazasulfuron or sulfosulfuron; an imidazolinone compound such as imazapyr, imazapyr-isopropylammonium or imazapic; a pyrimidinylsalicylic acid compound such as bispyribac-sodium; a dinitroaniline compound such as oryzalin or prodiamine; benazolin; benazolin-ethyl; diflufenzopyr; diflufenzopyr-sodium; chlorfiurenol; chlorfiurenol-methyl; pentanochior; butafenacil; glyphosate; glyphosate-sodium; glyphosate-potassium; glyphosate-ammonium; glyphosate-diammonium; glyphosate-isopropylammonium; glyphosate-trimesium; glyphosate-sesquisodium; glufosinate; glufosinate-ammonium; glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, bilanafos; bilanafos-sodium; asulam; asulam-sodium; dalapon; dalapon-sodium; TCA-sodium; trichloroacetic acid; CMA; fosamine; fosamine-ammonium; ammonium sulfamate; borax; chloroacetic acid; sodium chloroacete; methylarsonic acid; dimethylarsinic acid; sodium dimethylarsinate; flupropanate; flupropanate-sodium; isoxaben; mefluidide; mefluidide-diolamine; pentachlorophenol; sodium pentachlorophenoxide or pentachlorophenol laurate may, for example, be used.

In the present invention, the mixing ratio of the compound Q to said other herbicidal compound cannot generally be defined, as it varies depending upon various conditions such as the type of the compound, the type of the formulation, the weather conditions, and the type and the growth state of the plants to be controlled, but it is usually from 1:2,000 to 1,000:1, preferably from 1:1,500 to 100:1, more preferably from 1:1,200 to 30:1 by the weight ratio.

Said other herbicidal compound in the present invention is not particularly limited to a specific compound, and the mixing ratio with the compound Q is not limited to a specific range, but as one embodiment of the present invention, mixing ratios of the compound Q to some compounds are exemplified. However, the ratio may also vary depending upon various conditions such as the type of the compound, the type of formulation, the weather conditions, and the type and the growth state of the plants to be controlled as described above.

In a case where said other herbicidal compound is a phenoxy compound, the mixing ratio of (a) the compound Q to (b) the phenoxy compound is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:5 to 1:50 by the weight ratio. In a case where said other herbicidal compound is an aromatic carboxylic acid compound, the mixing ratio of (a) the compound Q to (b) the aromatic carboxylic acid compound is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:5 to 1:70 by the weight ratio.

In a case where said other herbicidal compound is fluoroxypyr, the mixing ratio of (a) the compound Q to (b) fluoroxypyr is usually from 1:1: to 1:500, preferably from 1:1 to 1:100, more preferably from 1:5 to 1:50 by the weight ratio.

In a case where said other herbicidal compound is a triazine compound, the mixing ratio of (a) the compound Q to (b) the triazine compound is usually from 1:2,000 to 1,000:1, preferably from 1:1,500 to 10:1, more preferably from 1:1,200 to 5:1 by the weight ratio.

In a case where said other herbicidal compound is a urea compound, the mixing ratio of (a) the compound Q to (b) the urea compound is usually from 1:1 to 1:500, preferably from 1:5 to 1:200, more preferably from 1:20 to 1:60 by the weight ratio.

In a case where said other herbicidal compound is a hydroxybenzonitrile compound, the mixing ratio of (a) the compound Q to (b) the hydroxybenzonitrile compound is usually from 1:500 to 50:1, preferably from 1:100 to 20:1, more preferably from 1:40 to 6:1 by the weight ratio. In a case where said other herbicidal compound is bentazone or its salt (such as bentazone-sodium), the mixing ratio of (a) the compound Q to (b) bentazone or its salt is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:1 to 1:40 by the weight ratio.

In a case where said other herbicidal compound is a diphenylether compound, the mixing ratio of (a) the compound Q to (b) the diphenylether compound is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:5 to 1:30 by the weight ratio.

In a case where said other herbicidal compound is a cyclic imide compound, the mixing ratio of (a) the compound Q to (b) the cyclic imide compound is usually from 1:50 to 100:1, preferably from 1:50 to 50:1, more preferably from 1:10 to 20:1 by the weight ratio.

In a case where said other herbicidal compound is carfentrazone-ethyl, the mixing ratio of (a) the compound Q to (b) carfentrazone-ethyl is usually from 1:100 to 100:1, preferably from 1:20 to 10:1, more preferably from 1:10 to 10:1 by the weight ratio.

In a case where said other herbicidal compound is pyridate, the mixing ratio of (a) the compound Q to (b) pyridate is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:10 to 1:40 by the weight ratio. In a case where said other herbicidal compound is sulcotrione, the mixing ratio of (a) the compound 0 to (b) sulcotrione is usually from 1:100 to 10:1, preferably from 1:10 to 10:1, more preferably from 1:5 to 2:1 by the weight ratio.

In a case where said other herbicidal compound is mesotrione, the mixing ratio of (a) the compound Q to (b) mesotrione is usually from 1:1 to 1:100, preferably from 1:1 to 1:50, more preferably from 1:1 to 1:10 by the weight ratio.

In a case where said other herbicidal compound is a sulfonylurea compound, the mixing ratio of (a) the compound Q to (b) the sulfonylurea compound is usually from 1:100 to 100:1, preferably from 1:70 to 50:1, more preferably from 1:50 to 30:1 by the weight ratio.

In a case where said other herbicidal compound is a triazolopyrimidinesulfonamide compound, the mixing ratio of (a) the compound Q to (b) the triazolopyrimidinesulfonamide compound is usually from 1:100 to 100:1, preferably from 1:50 to 10:1, more preferably from 1:10 to 5:1 by the weight ratio.

In a case where said other herbicidal compound is an imidazolinone compound, the mixing ratio of (a) the compound Q to (b) the imidazolinone compound is usually from 1:100 to 100:1, preferably from 1:50 to 10:1, more preferably from 1:10 to 5:1 by the weight ratio.

In a case where said other herbicidal compound is glyphosate or its salt (such as glyphosate-ammonium), the mixing ratio of (a) the compound Q to (b) glyphosate or its salt is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:1 to 1:80 by the weight ratio.

In a case where said other herbicidal compound is glufosinate, glufosinate-P or its salt (such as glufosinate-ammonium, glufosinate-P-ammonium), the mixing ratio of (a) the compound Q to (b) glufosinate, glufosinate-P or its salt is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:1 to 1:40 by the weight ratio.

In a case where said other herbicidal compound is a dinitrianiline compound, the mixing ratio of (a) the compound Q to (b) the dinitrianiline compound is usually from 1:1 to 1:1,000, preferably from 1:1 to 1:100, more preferably from 1:1 to 1:50 by the weight ratio.

In a case where said other herbicidal compound is a chloroacetamide compound, the mixing ratio of (a) the compound Q to (b) the chloroacetamide compound is usually from 1:1 to 1:1,000, preferably from 1:1 to 1:500, more preferably from 1:1 to 1:300 by the weight ratio.

In a case where said other herbicidal compound is flufenacet, the mixing ratio of (a) the compound Q to (b) flufenacet is usually from 1:1 to 1:500, preferably from 1:5 to 1:100, more preferably from 1:15 to 1:50 by the weight ratio.

In a case where said other herbicidal compound is pyroxasulfone, the mixing ratio of (a) the compound Q to (b) pyroxasulfone is usually from 1:1 to 1:500, preferably from 1:1 to 1:100, more preferably from 1:1 to 1:50 by the weight ratio.

The dose of the herbicidally active ingredients in the present invention cannot generally be defined, as it varies depending upon various conditions such as the types of the compound Q and other herbicidal compound, their mixing ratio, the type of the formulation, the weather conditions, and the type and the growth state of the plants to be controlled. However, the compound Q is applied in an amount of usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha, more preferably from 1 to 1,000 g/ha, and said other herbicidal compound is applied in an amount of usually from 0.1 to 50,000 g/ha, preferably from 1 to 10,000 g/ha, more preferably from 1.5 to 10,000 g/ha, and the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 60,000 g/ha, preferably from 2 to 12,000 g/ha, more preferably from 2.5 to 11,000 g/ha.

Said other herbicidal compound in the present invention is not limited to a specific compound, and its dose is not limited to a specific range, but as one embodiment of the present invention, doses of some compounds are exemplified. However, the dose may vary depending upon various conditions such as the type of the compound, the type of the formulation, the weather conditions, and the type and the growth state of the plants to be controlled in some cases as described above.

In a case where other herbicidal compound is a phenoxy compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is an aromatic carboxylic acid compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is fluoroxypyr, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is a triazine compound, the dose of said other herbicidal compound is usually from 0.1 to 50,000 g/ha, preferably from 10 to 10,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 60,000 g/ha, preferably from 11 to 12,000 g/ha.

In a case where other herbicidal compound is a urea compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is a hydroxybenzonitrile compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is bentazone or its salt (such as bentazone-sodium), the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is a diphenylether compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is a cyclic imide compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is carfentrazone-ethyl, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is pyridate, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is sulcotrione, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is mesotrione, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is a sulfonylurea compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 500 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 2,500 g/ha.

In a case where other herbicidal compound is a triazolopyrimidinesulfonamide compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is an imidazolinone compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is glyphosate or its salt (such as glyphosate-ammonium), the dose of said other herbicidal compound is usually from 0.1 to 50,000 g/ha, preferably from 1 to 5,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 60,000 g/ha, preferably from 2 to 7,000 g/ha.

In a case where other herbicidal compound is glufosinate, glufosinate-P or its salt (such as glufosinate-ammonium, glufosinate-P-ammonium), the dose of said other herbicidal compound is usually from 0.1 to 50,000 g/ha, preferably from 1 to 5,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 60,000 g/ha, preferably from 2 to 7,000 g/ha.

In a case where other herbicidal compound is a dinitroaniline compound, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 5,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 7,000 g/ha.

In a case where other herbicidal compound is a chloroacetamide compound, the dose of said other herbicidal compound is usually from 0.1 to 50,000 g/ha, preferably from 1 to 10,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 60,000 g/ha, preferably from 2 to 12,000 g/ha.

In a case where other herbicidal compound is flufenacet, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

In a case where other herbicidal compound is pyroxasulfone, the dose of said other herbicidal compound is usually from 0.1 to 10,000 g/ha, preferably from 1 to 2,000 g/ha. Further, the appropriate dose of the compound Q and said other herbicidal compound in total is usually from 0.2 to 20,000 g/ha, preferably from 2 to 4,000 g/ha.

With respect to application, application to undesired plants or application to a place where they grow (either before or after emerging of the plants) may optionally be selected. Further, the compound Q and other herbicidal compound may separately be formulated so that they are mixed for use at the time of application, or they may be formulated together. As examples of a specific application method, the following may be mentioned.

1. The compound Q and other herbicidal compound are formulated together, and the formulation is applied as it is.

2. The compound Q and other herbicidal compound are formulated together, the formulation is diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.

3. The compound Q and other herbicidal compound are separately formulated and applied as they are.

4. The compound Q and other herbicidal compound are separately formulated, and they are diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.

5. The compound Q and other herbicidal compound are separately formulated, and the formulations are mixed when diluted to a predetermined concentration with e.g. water, and as the case requires, a spreader (such as a surfactant, a vegetable oil or a mineral oil) is added for application.

The herbicidal composition of the present invention may be prepared by mixing the compound Q and other herbicidal compound, as active ingredients, with various agricultural additives in accordance with conventional formulation methods for agricultural chemicals, and applied in the form of various formulations such as dusts, granules, water dispersible granules, wettable powders, tablets, pills, capsules (including a formulation packaged by a water soluble film), water-based suspensions, oil-based suspensions, microemulsions, suspoemulsions, water soluble powders, emulsifiable concentrates, soluble concentrates or pastes. It may be formed into any formulation which is commonly used in this field, so long as the object of the present invention is thereby met.

At the time of the formulation, the compound Q and other herbicidal compound may be mixed together for the formulation, or they may be separately formulated.

The additives to be used for the formulation include, for example, a solid carrier such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite or starch; a solvent such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethylsulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone or an alcohol; an anionic surfactant or spreader such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenylether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, a salt of polyoxyethylene aryl ether phosphoric acid ester, a naphthalene sulfonate condensed with formaldehyde or an alkylnaphthalene sulfonate condensed with formaldehyde; a nonionic surfactant or spreader such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, polyethylene glycol, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil or a polyoxypropylene fatty acid ester; and a vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil or liquid paraffins. These additives may suitably be selected for use alone or in combination as a mixture of two or more of them, so long as the object of the present invention is met. Further, additives other than the above-mentioned may be suitably selected for use among those known in this field. For example, various additives commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a safener, an anti-mold agent, a bubble agent, a disintegrator and a binder, may be used. The mix ratio by weight of the compound Q or other herbicidal compound to such various additives may be from 0.1:99.9 to 95:5, preferably from 0.2:99.8 to 85:15.

The herbicidal composition of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity-reducing agents, whereby synergistic effects or activities may sometimes be obtained. Such other agricultural chemicals include, for example, a fungicide, an antibiotic, a plant hormone and an insecticide.

Now, examples of preferred embodiments of the present invention will be given below, but it should be understood that the present invention is by no means restricted thereto.

(1) A herbicidal composition comprising as active ingredients (a) a herbicidal benzoylpyrazole compound of the formula (I) or its salt wherein R¹ is alkyl, R² is a hydrogen atom or alkyl, R³ is alkyl, R⁴ is alkyl or halogen, R⁵ is alkoxyalkyl, haloalkoxyalkyl, alkoxy, haloalkoxy, alkoxyalkoxy or —C(O)OR⁷, R⁶ is alkylsulfonyl, A is alkylene substituted by at least one alkyl, and R⁷ is alkyl, and (b) other herbicidal compound.

(2) A herbicidal composition comprising as active ingredients (a) a herbicidal benzoylpyrazole compound of the formula (I) or its salt wherein R¹ is alkyl, R² is a hydrogen atom, R³ is alkyl, R⁴ is alkyl, R⁵ is alkoxyalkyl, alkoxy, alkoxyalkoxy or —C(O)OR⁷, R⁶ is alkylsulfonyl, A is alkylene substituted by at least one alkyl, and R⁷ is alkyl, and (b) other herbicidal compound.

(3) A herbicidal composition comprising as active ingredients (a) a herbicidal benzoylpyrazole compound of the formula (I) or its salt wherein R¹ is alkyl, R² is a hydrogen atom, R³ is alkyl, R⁴ is alkyl, R⁵ is alkoxyalkoxy, R⁶ is alkylsulfonyl, and A is alkylene substituted by at least one alkyl, and (b) other herbicidal compound.

(4) A herbicidal composition comprising as active ingredients (a) a herbicidal benzoylpyrazole compound of the formula (I) or its salt wherein R¹ is —CH₃ or —CH₂CH₃, R² is —H, R³ is —CH₃ or —CH₂CH₃, R⁴ is —CH₃, R⁵ is —OCH2CH2OCH3, R⁶ is —SO₂CH₃ and A is —CH(CH₃)—, and (b) other herbicidal compound.

Now, typical examples of the compound Q will be given in Table 1, but the compound Q in the present invention is not limited thereto. These compounds can be prepared in accordance with various processes disclosed in e.g. WO2007/069771 or WO2008/065907. Further, the after-mentioned Compound No. 4 may be prepared in accordance with the following Preparation Example.

Preparation Example Preparation of 1-(1-ethyl-4-(3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl)-1H-pyrazol-5-yloxy)ethyl methyl carbonate (the following Compound No. 4)

5-Hydroxy-1-ethylpyrazol-4-yl3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (300 mg) was dissolved in 2-butanone (10 mL), and potassium carbonate (130 mg) and tetrabutylammonium bromide (15 mg) were added. After stirring at room temperature for 10 minutes, 1-chloroethyl methyl carbonate (purity: 85%, 270 mg) was added at room temperature, followed by heating and refluxing for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and poured into water and then extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and a saturated sodium chloride aqueous solution, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography with n-hexane:ethyl acetate=1:1, to obtain the desired product (180 mg) as slightly yellow solid. The NMR spectrum data of this product are as follows.

¹H-NMR δppm (measuring instrument:JEOL-GSX (400 MHz), solvent:CDCl₃) 1.40 (3H, t, J=7.2 Hz), 1.77 (3H, d, J=5.2 Hz), 2.35 (3H, s), 2.94 (3H, s), 3.46 (3H, s), 3.71 (3H, s), 3.80 (211, t, J=4.4 Hz), 4.05 (2H, m), 4.24 (2H, t, J=4.4 Hz), 6.78 (1H, q, J=5.2 Hz), 7.26 (1H, d, J=7.6 Hz), 7.28 (1H, s), 7.88 (1H, d, J=7.6 Hz).

In Table 1, No. represents a Compound No. Further, in Table 1, Me represents a methyl group, Et an ethyl group, n-Pr a n-propyl group, i-Pr an isopropyl group, n-Bu a n-butyl group, and t-Bu a tertiary butyl group. Further, the left-hand side of -A- is bonded to the pyrazole side, and the right-hand side of -A- is bonded to the carbonate side.

TABLE 1 (I)

No. R¹ R² R³ R⁴ R⁵ R⁶ —A— [HYO 1] 1 Me H Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 2 Me H Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 3 Et H Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 4 Et H Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 5 Me H Et Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 6 Me H Et Me OCH₂CF₃ SO₂Me —CH(Me)— 7 Me H Et Me CH₂OMe SO₂Me —CH(Me)— 8 Me H Et Cl CH₂OMe SO₂Me —CH(Me)— 9 n-Bu H Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 10 t-Bu H Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 11 Me Me Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 12 Me H Et Me OCH₂CH₂OMe SO₂Me —C(Me)(Et)— 13 Me H Et Me OCH₂CH₂OMe SO₂Me —CH(Et)— 14 Me H Et Me OCH₂CH₂OMe SO₂Me —CH(i-Pr)— 15 Me H Et Me CH₂OCH₂CF₃ SO₂Me —CH(Me)— 16 Et H Et Cl C(O)OMe SO₂Me —CH(Me)— 17 Me H Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 18 i-Pr H Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 19 Me H n-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 20 Me H n-Bu Me OCH₂CH₂OMe SO₂Me —CH(Me)— 21 Me H Et Me C(O)OMe SO₂Me —CH(Me)— 22 Me H Me Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 23 Et H Et Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 24 Me H i-Pr Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 25 i-Pr Me Et Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 26 Me H n-Pr Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 27 Me H n-Bu Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 28 Me H Et Me OCH₂CH₂OMe SO₂Me —C(Me)₂— 29 Et H Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— [HYO 2] 30 t-Bu H Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 31 Me Me Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 32 Me H Me Me OCH₂CH₂OMe SO₂Et —CH(Me)— 33 Me H Et Me OCH₂CH₂OMe SO₂Et —CH(Me)— 34 Et H Et Me OCH₂CH₂OMe SO₂Et —CH(Me)— 35 Me H i-Pr Me OCH₂CH₂OMe SO₂Et —CH(Me)— 36 Me H Et Me OCH₂CH₂OMe SO₂Et —C(Me)₂— 37 Me H Et Me OCH₂CF₃ SO₂Et —CH(Me)— 38 Me H Et Me CH₂OMe SO₂Et —CH(Me)— 39 Me H Et Cl CH₂OMe SO₂Et —CH(Me)— 40 n-Bu H Et Me OCH₂CH₂OMe SO₂Et —CH(Me)— 41 t-Bu H Et Me OCH₂CH₂OMe SO₂Et —CH(Me)— 42 Me Me Et Me OCH₂CH₂OMe SO₂Et —CH(Me)— 43 Me H Et Me OCH₂CH₂OMe SO₂Et —C(Me(Et)— 44 Me H Et Me OCH₂CH₂OMe SO₂Et —CH(Et)— 45 Me H Et Me OCH₂CH₂OMe SO₂Et —CH(i-Pr)— 46 Me H Et Me CH₂OCH₂CF₃ SO₂Et —CH(Me)— 47 Et H Et Cl C(O)OMe SO₂Et —CH(Me)— 48 Me H Et Cl OCH₂CH₂OMe SO₂Et —CH(Me)— 49 i-Pr Me Et Me OCH₂CH₂OMe SO₂Et —CH(Me)— 50 Me H n-Pr Me OCH₂CH₂OMe SO₂Et —CH(Me)— 51 Me H n-Bu Me OCH₂CH₂OMe SO₂Et —CH(Me)— 52 Me H Et Me C(O)OMe SO₂Et —CH(Me)— 53 Me H Me Me OCH₂CH₂OMe SO₂Et —C(Me)₂— 54 Et H Et Me OCH₂CH₂OMe SO₂Et —C(Me)₂— 55 Me H i-Pr Me OCH₂CH₂OMe SO₂Et —C(Me)₂— 56 Me H Me Br OCH₂CH₂OMe SO₂Me —CH(Me)— 57 Me H Et Br OCH₂CH₂OMe SO₂Me —CH(Me)— 58 Et H Et Br OCH₂CH₂OMe SO₂Me —CH(Me)— 59 Me H i-Pr Br OCH₂CH₂OMe SO₂Me —CH(Me)— 60 Me H Et Br OCH₂CH₂OMe SO₂Me —C(Me)₂— 61 Me H Et Br OCH₂CF₃ SO₂Me —CH(Me)— 62 Me H Et Br CH₂OMe SO₂Me —CH(Me)— 63 n-Bu H Et Me OCH₂CH₂OMe SO₂Et —CH(Me)— 64 t-Bu H i-Pr Me OCH₂CH₂OMe SO₂Et —CH(Me)— 65 Me Me i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 66 Me Et Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— [HYO 3] 67 Me Et Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 68 Me Et i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 69 Me Et n-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 70 Me Et n-Bu Me OCH₂CH₂OMe SO₂Me —CH(Me)— 71 Et Et Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 72 Et Et Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 73 Et Et i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 74 Et Et n-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 75 Et Et n-Bu Me OCH₂CH₂OMe SO₂Me —CH(Me)— 76 i-Pr Et Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 77 i-Pr Et Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 78 i-Pr Et i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 79 i-Pr Et n-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 80 i-Pr Et n-Bu Me OCH₂CH₂OMe SO₂Me —CH(Me)— 81 n-Pr Et Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 82 n-Pr Et Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 83 n-Pr Et i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 84 n-Pr Et n-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 85 n-Pr Et n-Bu Me OCH₂CH₂OMe SO₂Me —CH(Me)— 86 n-Bu Et Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 87 n-Bu Et Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 88 n-Bu Et i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 89 n-Bu Et n-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 90 n-Bu Et n-Bu Me OCH₂CH₂OMe SO₂Me —CH(Me)— 91 t-Bu Et Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 92 t-Bu Et Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 93 t-Bu Et i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 94 t-Bu Et n-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 95 t-Bu Et n-Bu Me OCH₂CH₂OMe SO₂Me —CH(Me)— 96 Me Et Me Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 97 Me Et Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 98 Me Et i-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 99 Me Et n-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 100 Me Et n-Bu Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 101 Et Et Me Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 102 Et Et Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 103 Et Et i-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 104 Et Et n-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— [HYO 4] 105 Et Et n-Bu Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 106 i-Pr Et Me Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 107 i-Pr Et Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 108 i-Pr Et i-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 109 i-Pr Et n-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 110 i-Pr Et n-Bu Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 111 n-Pr Et Me Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 112 n-Pr Et Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 113 n-Pr Et i-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 114 n-Pr Et n-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 115 n-Pr Et n-Bu Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 116 n-Bu Et Me Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 117 n-Bu Et Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 118 n-Bu Et i-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 119 n-Bu Et n-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 120 n-Bu Et n-Bu Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 121 t-Bu Et Me Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 122 t-Bu Et Et Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 123 t-Bu Et i-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 124 t-Bu Et n-Pr Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 125 t-Bu Et n-Bu Cl OCH₂CH₂OMe SO₂Me —CH(Me)— 126 Me Et Me Me OCH₂CF₃ SO₂Me —CH(Me)— 127 Me Et Et Me OCH₂CF₃ SO₂Me —CH(Me)— 128 Me Et i-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 129 Me Et n-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 130 Me Et n-Bu Me OCH₂CF₃ SO₂Me —CH(Me)— 131 Et Et Me Me OCH₂CF₃ SO₂Me —CH(Me)— 132 Et Et Et Me OCH₂CF₃ SO₂Me —CH(Me)— 133 Et Et i-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 134 Et Et n-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 135 Et Et n-Bu Me OCH₂CF₃ SO₂Me —CH(Me)— 136 i-Pr Et Me Me OCH₂CF₃ SO₂Me —CH(Me)— 137 i-Pr Et Et Me OCH₂CF₃ SO₂Me —CH(Me)— 138 i-Pr Et i-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 139 i-Pr Et n-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 140 i-Pr Et n-Bu Me OCH₂CF₃ SO₂Me —CH(Me)— 141 n-Pr Et Me Me OCH₂CF₃ SO₂Me —CH(Me)— 142 n-Pr Et Et Me OCH₂CF₃ SO₂Me —CH(Me)— [HYO 5] 143 n-Pr Et i-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 144 n-Pr Et n-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 145 n-Pr Et n-Bu Me OCH₂CF₃ SO₂Me —CH(Me)— 146 n-Bu Et Me Me OCH₂CF₃ SO₂Me —CH(Me)— 147 n-Bu Et Et Me OCH₂CF₃ SO₂Me —CH(Me)— 148 n-Bu Et i-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 149 n-Bu Et n-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 150 n-Bu Et n-Bu Me OCH₂CF₃ SO₂Me —CH(Me)— 151 t-Bu Et Me Me OCH₂CF₃ SO₂Me —CH(Me)— 152 t-Bu Et Et Me OCH₂CF₃ SO₂Me —CH(Me)— 153 t-Bu Et i-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 154 t-Bu Et n-Pr Me OCH₂CF₃ SO₂Me —CH(Me)— 155 t-Bu Et n-Bu Me OCH₂CF₃ SO₂Me —CH(Me)— 156 Me Et Me Cl OCH₂CF₃ SO₂Me —CH(Me)— 157 Me Et Et Cl OCH₂CF₃ SO₂Me —CH(Me)— 158 Me Et i-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 159 Me Et n-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 160 Me Et n-Bu Cl OCH₂CF₃ SO₂Me —CH(Me)— 161 Et Et Me Cl OCH₂CF₃ SO₂Me —CH(Me)— 162 Et Et Et Cl OCH₂CF₃ SO₂Me —CH(Me)— 163 Et Et i-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 164 Et Et n-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 165 Et Et n-Bu Cl OCH₂CF₃ SO₂Me —CH(Me)— 166 i-Pr Et Me Cl OCH₂CF₃ SO₂Me —CH(Me)— 167 i-Pr Et Et Cl OCH₂CF₃ SO₂Me —CH(Me)— 168 i-Pr Et i-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 169 i-Pr Et n-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 170 i-Pr Et n-Bu Cl OCH₂CF₃ SO₂Me —CH(Me)— 171 n-Pr Et Me Cl OCH₂CF₃ SO₂Me —CH(Me)— 172 n-Pr Et Et Cl OCH₂CF₃ SO₂Me —CH(Me)— 173 n-Pr Et i-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 174 n-Pr Et n-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 175 n-Pr Et n-Bu Cl OCH₂CF₃ SO₂Me —CH(Me)— 176 n-Bu Et Me Cl OCH₂CF₃ SO₂Me —CH(Me)— 177 n-Bu Et Et Cl OCH₂CF₃ SO₂Me —CH(Me)— 178 n-Bu Et i-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 179 n-Bu Et n-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 180 n-Bu Et n-Bu Cl OCH₂CF₃ SO₂Me —CH(Me)— [HYO 6] 181 t-Bu Et Me Cl OCH₂CF₃ SO₂Me —CH(Me)— 182 t-Bu Et Et Cl OCH₂CF₃ SO₂Me —CH(Me)— 183 t-Bu Et i-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 184 t-Bu Et n-Pr Cl OCH₂CF₃ SO₂Me —CH(Me)— 185 t-Bu Et n-Bu Cl OCH₂CF₃ SO₂Me —CH(Me)— 186 Me Et Me Me CH₂OMe SO₂Me —CH(Me)— 187 Me Et Et Me CH₂OMe SO₂Me —CH(Me)— 188 Me Et i-Pr Me CH₂OMe SO₂Me —CH(Me)— 189 Me Et n-Pr Me CH₂OMe SO₂Me —CH(Me)— 190 Me Et n-Bu Me CH₂OMe SO₂Me —CH(Me)— 191 Et Et Me Me CH₂OMe SO₂Me —CH(Me)— 192 Et Et Et Me CH₂OMe SO₂Me —CH(Me)— 193 Et Et i-Pr Me CH₂OMe SO₂Me —CH(Me)— 194 Et Et n-Pr Me CH₂OMe SO₂Me —CH(Me)— 195 Et Et n-Bu Me CH₂OMe SO₂Me —CH(Me)— 196 i-Pr Et Me Me CH₂OMe SO₂Me —CH(Me)— 197 i-Pr Et Et Me CH₂OMe SO₂Me —CH(Me)— 198 i-Pr Et i-Pr Me CH₂OMe SO₂Me —CH(Me)— 199 i-Pr Et n-Pr Me CH₂OMe SO₂Me —CH(Me)— 200 i-Pr Et n-Bu Me CH₂OMe SO₂Me —CH(Me)— 201 n-Pr Et Me Me CH₂OMe SO₂Me —CH(Me)— 202 n-Pr Et Et Me CH₂OMe SO₂Me —CH(Me)— 203 n-Pr Et i-Pr Me CH₂OMe SO₂Me —CH(Me)— 204 n-Pr Et n-Pr Me CH₂OMe SO₂Me —CH(Me)— 205 n-Pr Et n-Bu Me CH₂OMe SO₂Me —CH(Me)— 206 n-Bu Et Me Me CH₂OMe SO₂Me —CH(Me)— 207 n-Bu Et Et Me CH₂OMe SO₂Me —CH(Me)— 208 n-Bu Et i-Pr Me CH₂OMe SO₂Me —CH(Me)— 209 n-Bu Et n-Pr Me CH₂OMe SO₂Me —CH(Me)— 210 n-Bu Et n-Bu Me CH₂OMe SO₂Me —CH(Me)— 211 t-Bu Et Me Me CH₂OMe SO₂Me —CH(Me)— 212 t-Bu Et Et Me CH₂OMe SO₂Me —CH(Me)— 213 t-Bu Et i-Pr Me CH₂OMe SO₂Me —CH(Me)— 214 t-Bu Et n-Pr Me CH₂OMe SO₂Me —CH(Me)— 215 t-Bu Et n-Bu Me CH₂OMe SO₂Me —CH(Me)— 216 Me Et Me Cl CH₂OMe SO₂Me —CH(Me)— [HYO 7] 217 Me Et Et Cl CH₂OMe SO₂Me —CH(Me)— 218 Me Et i-Pr Cl CH₂OMe SO₂Me —CH(Me)— 219 Me Et n-Pr Cl CH₂OMe SO₂Me —CH(Me)— 220 Me Et n-Bu Cl CH₂OMe SO₂Me —CH(Me)— 221 Et Et Me Cl CH₂OMe SO₂Me —CH(Me)— 222 Et Et Et Cl CH₂OMe SO₂Me —CH(Me)— 223 Et Et i-Pr Cl CH₂OMe SO₂Me —CH(Me)— 224 Et Et n-Pr Cl CH₂OMe SO₂Me —CH(Me)— 225 Et Et n-Bu Cl CH₂OMe SO₂Me —CH(Me)— 226 i-Pr Et Me Cl CH₂OMe SO₂Me —CH(Me)— 227 i-Pr Et Et Cl CH₂OMe SO₂Me —CH(Me)— 228 i-Pr Et i-Pr Cl CH₂OMe SO₂Me —CH(Me)— 229 i-Pr Et n-Pr Cl CH₂OMe SO₂Me —CH(Me)— 230 i-Pr Et n-Bu Cl CH₂OMe SO₂Me —CH(Me)— 231 n-Pr Et Me Cl CH₂OMe SO₂Me —CH(Me)— 232 n-Pr Et Et Cl CH₂OMe SO₂Me —CH(Me)— 233 n-Pr Et i-Pr Cl CH₂OMe SO₂Me —CH(Me)— 234 n-Pr Et n-Pr Cl CH₂OMe SO₂Me —CH(Me)— 235 n-Pr Et n-Bu Cl CH₂OMe SO₂Me —CH(Me)— 236 n-Bu Et Me Cl CH₂OMe SO₂Me —CH(Me)— 237 n-Bu Et Et Cl CH₂OMe SO₂Me —CH(Me)— 238 n-Bu Et i-Pr Cl CH₂OMe SO₂Me —CH(Me)— 239 n-Bu Et n-Pr Cl CH₂OMe SO₂Me —CH(Me)— 240 n-Bu Et n-Bu Cl CH₂OMe SO₂Me —CH(Me)— 241 t-Bu Et Me Cl CH₂OMe SO₂Me —CH(Me)— 242 t-Bu Et Et Cl CH₂OMe SO₂Me —CH(Me)— 243 t-Bu Et i-Pr Cl CH₂OMe SO₂Me —CH(Me)— 244 t-Bu Et n-Pr Cl CH₂OMe SO₂Me —CH(Me)— 245 t-Bu Et n-Bu Cl CH₂OMe SO₂Me —CH(Me)— 246 Me Et Me Me CH₂OMe SO₂Me —CH(Me)— 247 Me Et Et Me CH₂OMe SO₂Me —CH(Me)— 248 Me Et i-Pr Me CH₂OMe SO₂Me —CH(Me)— 249 Me Et n-Pr Me CH₂OMe SO₂Me —CH(Me)— 250 Me Et n-Bu Me CH₂OMe SO₂Me —CH(Me)— 251 Et Et Me Me CH₂OMe SO₂Me —CH(Me)— [HYO 8] 252 Et Et Et Me C(O)OMe SO₂Me —CH(Me)— 253 Et Et i-Pr Me C(O)OMe SO₂Me —CH(Me)— 254 Et Et n-Pr Me C(O)OMe SO₂Me —CH(Me)— 255 Et Et n-Bu Me C(O)OMe SO₂Me —CH(Me)— 256 i-Pr Et Me Me C(O)OMe SO₂Me —CH(Me)— 257 i-Pr Et Et Me C(O)OMe SO₂Me —CH(Me)— 258 i-Pr Et i-Pr Me C(O)OMe SO₂Me —CH(Me)— 259 i-Pr Et n-Pr Me C(O)OMe SO₂Me —CH(Me)— 260 i-Pr Et n-Bu Me C(O)OMe SO₂Me —CH(Me)— 261 n-Pr Et Me Me C(O)OMe SO₂Me —CH(Me)— 262 n-Pr Et Et Me C(O)OMe SO₂Me —CH(Me)— 263 n-Pr Et i-Pr Me C(O)OMe SO₂Me —CH(Me)— 264 n-Pr Et n-Pr Me C(O)OMe SO₂Me —CH(Me)— 265 n-Pr Et n-Bu Me C(O)OMe SO₂Me —CH(Me)— 266 n-Bu Et Me Me C(O)OMe SO₂Me —CH(Me)— 267 n-Bu Et Et Me C(O)OMe SO₂Me —CH(Me)— 268 n-Bu Et i-Pr Me C(O)OMe SO₂Me —CH(Me)— 269 n-Bu Et n-Pr Me C(O)OMe SO₂Me —CH(Me)— 270 n-Bu Et n-Bu Me C(O)OMe SO₂Me —CH(Me)— 271 t-Bu Et Me Me C(O)OMe SO₂Me —CH(Me)— 272 t-Bu Et Et Me C(O)OMe SO₂Me —CH(Me)— 273 t-Bu Et i-Pr Me C(O)OMe SO₂Me —CH(Me)— 274 t-Bu Et n-Pr Me C(O)OMe SO₂Me —CH(Me)— 275 t-Bu Et n-Bu Me C(O)OMe SO₂Me —CH(Me)— 276 Me Et Me Cl C(O)OMe SO₂Me —CH(Me)— 277 Me Et Et Cl C(O)OMe SO₂Me —CH(Me)— 278 Me Et i-Pr Cl C(O)OMe SO₂Me —CH(Me)— 279 Me Et n-Pr Cl C(O)OMe SO₂Me —CH(Me)— 280 Me Et n-Bu Cl C(O)OMe SO₂Me —CH(Me)— 281 Et Et Me Cl C(O)OMe SO₂Me —CH(Me)— 282 Et Et Et Cl C(O)OMe SO₂Me —CH(Me)— 283 Et Et i-Pr Cl C(O)OMe SO₂Me —CH(Me)— 284 Et Et n-Pr Cl C(O)OMe SO₂Me —CH(Me)— 285 Et Et n-Bu Cl C(O)OMe SO₂Me —CH(Me)— 286 i-Pr Et Me Cl C(O)OMe SO₂Me —CH(Me)— 287 i-Pr Et Et Cl C(O)OMe SO₂Me —CH(Me)— [HYO 9] 288 i-Pr Et i-Pr Cl C(O)OMe SO₂Me —CH(Me)— 289 i-Pr Et n-Pr Cl C(O)OMe SO₂Me —CH(Me)— 290 i-Pr Et n-Bu Cl C(O)OMe SO₂Me —CH(Me)— 291 n-Pr Et Me Cl C(O)OMe SO₂Me —CH(Me)— 292 n-Pr Et Et Cl C(O)OMe SO₂Me —CH(Me)— 293 n-Pr Et i-Pr Cl C(O)OMe SO₂Me —CH(Me)— 294 n-Pr Et n-Pr Cl C(O)OMe SO₂Me —CH(Me)— 295 n-Pr Et n-Bu Cl C(O)OMe SO₂Me —CH(Me)— 296 n-Bu Et Me Cl C(O)OMe SO₂Me —CH(Me)— 297 n-Bu Et Et Cl C(O)OMe SO₂Me —CH(Me)— 298 n-Bu Et i-Pr Cl C(O)OMe SO₂Me —CH(Me)— 299 n-Bu Et n-Pr Cl C(O)OMe SO₂Me —CH(Me)— 300 n-Bu Et n-Bu Cl C(O)OMe SO₂Me —CH(Me)— 301 t-Bu Et Me Cl C(O)OMe SO₂Me —CH(Me)— 302 t-Bu Et Et Cl C(O)OMe SO₂Me —CH(Me)— 303 t-Bu Et i-Pr Cl C(O)OMe SO₂Me —CH(Me)— 304 t-Bu Et n-Pr Cl C(O)OMe SO₂Me —CH(Me)— 305 t-Bu Et n-Bu Cl C(O)OMe SO₂Me —CH(Me)— 306 Me H Et Me CH₂OCH(Me)₂ SO₂Me —CH(Me)— 307 Et H Et Me CH₂OCH(Me)₂ SO₂Me —CH(Me)— 308 n-Pr H Et Me CH₂OCH(Me)₂ SO₂Me —CH(Me)— 309 i-Pr H Et Me CH₂OCH(Me)₂ SO₂Me —CH(Me)— 310 Me H Et Cl CH₂OCH(Me)₂ SO₂Me —CH(Me)— 311 Et H Et Cl CH₂OCH(Me)₂ SO₂Me —CH(Me)— 312 n-Pr H Et Cl CH₂OCH(Me)₂ SO₂Me —CH(Me)— 313 i-Pr H Et Cl CH₂OCH(Me)₂ SO₂Me —CH(Me)— 314 Me H Me Me CH₂OEt SO₂Me —CH(Me)— 315 Me H Me Me C(O)OMe SO₂Me —CH(Me)— 316 Me H Me Me CH₂OMe SO₂Me —CH(Me)— 317 Me H Et Me CH₂OEt SO₂Me —CH(Me)— 318 Me H Et Me OCH₂CH₂OCH(Me)₂ SO₂Me —CH(Me)— 319 Me Me Me Me OCH₂CH₂OMe SO₂Me —CH(Me)— 320 Me H i-Pr Me OCH₂CH₂OMe SO₂Me —CH(Me)— 321 Et H Et Me C(O)OMe SO₂Me —CH(Me)— 322 Et Me Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 323 n-Pr H Et Me OCH₂CH₂OMe SO₂Me —CH(Me)— 324 i-Pr H Me Me OCH₂CH₂OMe SO₂Me —CH(Me)—

EXAMPLE(S) Example 1

Upland field soil was put into a 1/1,000,000 hectare pot, and seeds of various plants were sown. When the respective plants reached predetermined leaf stage, herbicidal compositions in predetermined amounts were diluted with water in an amount corresponding to 300 L/ha and applied for foliar treatment by a small sprayer.

On the 7 to 24 days after treatment, the state of growth of the respective plants was visually observed to determine the growth inhibition rate (measured value) in accordance with the following evaluation standard. Further, in accordance with the above Colby's formula, the growth inhibition rate (calculated value) was calculated. The results are shown in Tables 2-1 to 2-119. In Tables, with respect to the compound Q, Compound Nos. in Table 1 are described, and with respect to other herbicidal compounds, common names are described.

Growth inhibition rate (%)=0: equivalent to the non-treated area to 100: complete kill

TABLE 2-1 [HYO 10] Growth inhibition rate (%) of crabgrass (3.5 to 4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 78 — Nicosulfuron 10 30 — NO. 1 + 5 + 10 85 84.6 nicosulfuron

TABLE 2-2 [HYO 11] Growth inhibition rate (%) of prickly sida (2.1 to 3.1 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1 50 45 — Nicosulfuron 50 70 — 30 50 — 20 40 — 10 10 —  5 0 —  2.5 0 — NO. 1 + 50 + 50 85 84 nicosulfuron 50 + 30 85 73 50 + 20 78 67 50 + 10 65 51 50 + 5 75 45 50 + 2.5 65 45

TABLE 2-3 [HYO 12] Growth inhibition rate (%) of crabgrass (3.5 to 4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 78 — Atrazine 175 0 — NO. 1 + 5 + 175 99 78 atrazine

TABLE 2-4 [HYO 13] Growth inhibition rate (%) of velvetleaf (3.0-3.8 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1 5 88 — Atrazine 175 0 — NO. 1 + 5 + 175 97 88 atrazine

TABLE 2-5 [HYO 14] Growth inhibition rate (%) of crabgrass (3.5 to 4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 78 — Terbuthylazine 175 0 — NO. 1 + 5 + 175 94 78 terbuthylazine

TABLE 2-6 [HYO 15] Growth inhibition rate (%) of velvetleaf (3.0-3.8 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 88 — Terbuthylazine 175 0 — NO. 1 + 5 + 175 97 88 terbuthylazine

TABLE 2-7 [HYO 16] Growth inhibition rate (%) of crabgrass (3.5 to 4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 78 — Acetochlor 400 0 — NO. 1 + 5 + 400 93 78 acetochlor

TABLE 2-8 [HYO 17] Growth inhibition rate (%) of velvetleaf (3.0-3.8 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 88 — Acetochlor 400 0 — NO. 1 + 5 + 400 95 88 acetochlor

TABLE 2-9 [HYO 18] Growth inhibition rate (%) of crabgrass (3.5 to 4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 78 — S-Metolachlor 400 0 — NO. 1 + 5 + 400 88 78 S-metolachlor

TABLE 2-10 [HYO 19] Growth inhibition rate (%) of velvetleaf (3.0-3.8 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 1  5 88 — S-Metolachlor 400 0 — NO. 1 + 5 + 400 93 88 S-metolachlor

TABLE 2-11 [HYO 20] Growth inhibition rate (%) of crabgrass (4.5-5.1 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  1.875 40 — Nicosulfuron 80 94 — 20 50 — NO. 2 + 1.875 + 80 99 96 nicosulfuron 1.875 + 20 85 70

TABLE 2-12 [HYO 21] Growth inhibition rate (%) of velvetleaf (4.0-4.4 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  7 80 — Nicosulfuron 10 40 — NO. 2 + 7 + 10 95 88 nicosulfuron

TABLE 2-13 [HYO 22] Growth inhibition rate (%) of velvetleaf (4.0-4.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  1.875 40 — Nicosulfuron 80 83 — 60 70 — 40 65 — NO. 2 + 1.875 + 80 92 90 nicosulfuron 1.875 + 60 93 82 1.875 + 40 80 79

TABLE 2-14 [HYO 23] Growth inhibition rate (%) of crabgrass (3.1-4.0 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  15 85 — Atrazine 375 0 — NO 2 + 15 + 375 95 85 atrazine

TABLE 2-15 [HYO 24] Growth inhibition rate (%) of crabgrass (5.0-6.0 leaf stage) (14 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 3.75 60 — Atrazine 2000 25 — 1000 10 — 500 0 — NO. 2 + 3.75 + 2000 99 70 atrazine 3.75 + 1000 97 64 3.75 + 500  70 60

TABLE 2-16 [HYO 25] Growth inhibition rate (%) of velvetleaf (4.0-4.4 leaf stage) (22 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 15 85 — Atrazine 375 25 — NO. 2 + 15 + 375 100 89 atrazine

TABLE 2-17 [HYO 26] Growth inhibition rate (%) of velvetleaf (4.6-5.3 leaf stage) (14 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 1.875 65 — Atrazine 2000 70 — 1000 60 — 500 45 — NO 2 + 1.875 + 2000 100 90 atrazine 1.875 + 1000 100 86 1.875 + 500  100 81

TABLE 2-18 [HYO 27] Growth inhibition rate (%) of prickly sida (3.0-3.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 50 60 — Atrazine 250 65 — 125 45 — 63 30 — NO. 2 + 50 + 250 100 86 atrazine 50 + 125 100 78 50 + 63  100 72

TABLE 2-19 [HYO 28] Growth inhibition rate (%) of crabgrass Active (3.1-4.0 leaf stage) (22 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 15 85 — Terbuthylazine 375 0 — NO. 2 + 15 + 375 95 85 terbuthylazine

TABLE 2-20 [HYO 29] Growth inhibition rate (%) of velvetleaf Active (4.0-4.4 leaf stage) (22 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 80 — Terbuthylazine 175 15 — NO. 2 + 7 + 175 100 83 terbuthylazine

TABLE 2-21 [HYO 30] Growth inhibition rate (%) of velvetleaf Active (4.0-4.5 leaf stage) (21 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 3.75 55 — Terbuthylazine 2000 55 — 1000 45 — 500 30 — NO. 2 + 3.75 + 2000 100 80 terbuthylazine 3.75 + 1000 100 75 3.75 + 500  100 69

TABLE 2-22 [HYO 31] Growth inhibition rate (%) of prickly sida (3.0-4.0 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 100 35 — Terbuthylazine 250 20 — 125 0 — 63 0 — NO. 2 + 100 + 250 85 48 terbuthylazine 100 + 125 83 35 100 + 63  55 35

TABLE 2-23 [HYO 32] Growth inhibition rate (%) of prickly sida Active (3.0-3.3 leaf stage) (14 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 75 65 — Acetochlor 800 30 — 400 10 — 200 0 — 100 0 — NO. 2 + 75 + 800 80 76 acetochlor 75 + 400 83 69 75 + 200 70 65 75 + 100 80 65

TABLE 2-24 [HYO 33] Growth inhibition rate (%) of crabgrass Active (5.0-6.0 leaf stage) (14 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 3.75 60 — S-Metolachlor 800 0 — NO. 2 + 3.75 + 800 65 60 S-metolachlor

TABLE 2-25 [HYO 34] Growth inhibition rate (%) of velvetleaf Active (4.6-5.3 leaf stage) (14 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 15 88 — S-Metolachlor 1200 0 — NO. 2 + 15 + 1200 95 88 S-metolachlor

TABLE 2-26 [HYO 35] Growth inhibition rate (%) Active of prickly sida (3.0-3.3 leaf stage) ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 100 88 — S-Metolachlor 800 20 — NO. 2 + 100 + 800 100 90 S-metolachlor

TABLE 2-27 [HYO 36] Active Growth inhibition rate (%) of ingredient crabgrass (3.1-4.0 leaf stage) amount (22 days after treatment) Compound (g/ha) Measured value Calculated value NO. 2 7 68 — Bromoxynil-octanoate 77 0 — NO. 2 + 7 + 77 75 68 bromoxynil-octanoate

TABLE 2-28 [HYO 37] Active Growth inhibition rate (%) of ingredient velvetleaf (4.0-4.3 leaf stage) amount (22 days after treatment) Compound (g/ha) Measured value Calculated value NO. 2 3.75 0 — Bromoxynil-octanoate 100 25 — NO. 2 + 3.75 + 100 100 25 bromoxynil-octanoate

TABLE 2-29 [HYO 38] Active Growth inhibition rate (%) of ingredient pricky sida (3.0-3.3 leaf stage) amount (22 days after treatment) Compound (g/ha) Measured value Calculated value NO. 2 100 65 — Bromoxynil-octanoate 100 50 — 50 50 — 25 40 — NO. 2 +  100 + 100 100 80 bromoxynil-octanoate 100 + 50 100 80 100 + 25 94 76

TABLE 2-30 [HYO 39] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 53 — Clopyralid 300 0 — NO. 2 + 7 + 300 83 53 clopyralid

TABLE 2-31 [HYO 40] Growth inhibition rate (%) of velvetleaf (4.1-4.5 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 60 — Clopyralid 300 40 — NO. 2 + 7 + 300 88 76 clopyralid

TABLE 2-32 [HYO 41] Growth inhibition rate (%) of velvetleaf (3.5 to 4.3 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 95 — Linuron 250 85 — NO. 2 + 7 + 250 100 99.3 lunuron

TABLE 2-33 [HYO 42] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 53 — Prosulfuron 5 0 — NO. 2 + 7 + 5 89 53 prosulfuron

TABLE 2-34 [HYO 43] Growth inhibition rate (%) of velvetleaf (4.1-4.5 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 60 — Prosulfuron 5 90 — NO. 2 + 7 + 5 99 96 prosulfuron

TABLE 2-35 [HYO 44] Growth inhibition rate (%) of velvetleaf (3.5-4.3 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 95 — 2,4-D ethyl 100 80 — NO. 2 + 7 + 100 100 99 2,4-D ethyl

TABLE 2-36 [HYO 45] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 53 — Pyridate 200 0 — NO. 2 + 7 + 200 97 53 pyridate

TABLE 2-37 [HYO 46] Growth inhibition rate (%) of velvetleaf (4.1-4.5 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 70 — Pyridate 200 30 — NO. 2 + 7 + 200 90 79 pyridate

TABLE 2-38 [HYO 47] Growth inhibition rate (%) of crabgrass (4.4-5.0 leaf stage) Active ingredient (13 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 5 65 — Dicamba 100 0 — NO. 2 + 5 + 100 70 65 dicamba

TABLE 2-39 [HYO 48] Growth inhibition rate (%) of velvetleaf (3.3-4.2 leaf stage) Active ingredient (13 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 5 70 — Dicamba 100 35 — NO. 2 + 5 + 100 90 81 dicamba

TABLE 2-40 [HYO 49] Growth inhibition rate (%) of velvetleaf (3.5 to 4.3 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 15 97 — Glyphosate- 100 30 — ammonium NO. 2 + 15 + 100 99 98 glyphosate- ammonium

TABLE 2-41 [HYO 50] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 53 — Glufosinate- 100 0 — ammonium NO. 2 + 7 + 100 80 53 glufosinate- ammonium

TABLE 2-42 [HYO 51] Growth inhibition rate (%) of velvetleaf (4.1-4.5 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 60 — Glufosinate 200 10 — -ammonium NO. 2 + 7 + 200 88 64 glufosinate- ammonium

TABLE 2-43 [HYO 52] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 53 — Bentazone- 200 0 — sodium NO. 2 + 7 + 200 80 53 bentazone- sodium

TABLE 2-44 [HYO 53] Growth inhibition rate (%) of velvetleaf (4.1-4.5 leaf stage) Active ingredient (22 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2 7 60 — Bentazone- 100 0 — sodium NO. 2 + 7 + 100 100 60 bentazone- sodium

TABLE 2-45 [HYO 54] Growth inhibition rate (%) of crabgrass (4.4-5.0 leaf stage) Active ingredient (13 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  5 65 — Pethoxamid 200 0 — NO. 2 + 5 + 200 70 65 pethoxamid

TABLE 2-46 [HYO 55] Growth inhibition rate (%) of velvetleat (3.3-4.2 leaf stage) Active ingredient (13 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  5 70 — Pethoxamid 200 0 — NO. 2 + 5 + 200 90 70 pethoxamid

TABLE 2-47 [HYO 56] Growth inhibition rate (%) of velvetleaf (3.3-4.2 leaf stage) Active ingredient (13 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  5 70 — Pendimethalin 100 25 — NO. 2 + 5 + 100 90 78 pendimethalin

TABLE 2-48 [HYO 57] Growth inhibition rate (%) of crabgrass (4.4-5.0 leaf stage) Active ingredient (13 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  5 65 — Pyroxasulfone 50 0 — NO. 2 + 5 + 50 70 65 pyroxasulfone

TABLE 2-49 [HYO 58] Growth inhibition rate (%) of velvetleaf (3.3-4.2 leaf stage) Active ingredient (13 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 2  5 70 — Pyroxasulfone 50 5 — NO. 2 + 5 + 50 93 70 pyroxasulfone

TABLE 2-50 [HYO 59] Growth inhibition rate (%) of crabgrass (3.5-4.3 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 5 88 — Nicosulfuron 5 15 — NO. 3 + 5 + 5 92 90 nicosulfuron

TABLE 2-51 [HYO 60] Growth inhibition rate (%) of velvetleaf (3.1-3.4 leaf stage) Active ingredient (20 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 5 88 — Nicosulfuron 5 10 — NO. 3 + 5 + 5 94 89 nicosulfuron

TABLE 2-52 [HYO 61] Growth inhibition rate (%) of prickly sida (1.54-2.4 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 50 50 — Nicosulfuron 15 45 — NO. 3 + 50 + 15 75 73 nicosulfuron

TABLE 2-53 [HYO 62] Growth inhibition rate (%) of days after treatment (4.0-5.0 leaf Active ingredient stage) (21 days after treatment) Compound amount (g/ha) Measured value Calculated value No. 3  7 40 — Atrazine 125 0 — NO. 3 + 7 + 125 100 40 atrazine

TABLE 2-54 [HYO 63] Growth inhibition rate (%) of crabgrass (3.5 to 4.3 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3  5 88 — Terbuthylazine 300 25 — NO. 3 + 5 + 300 99 91 terbuthylazine

TABLE 2-55 [HYO 64] Growth inhibition rate (%) of velvetleaf (3.1-3.4 leaf stage) Active ingredient (20 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3  5 88 — Terbuthylazine 300 50 — NO. 3 + 5 + 300 100 94 terbuthylazine

TABLE 2-56 [HYO 65] Growth inhibition rate (%) of prickly side (1.5-2.4 leaf stage) Active ingredient (20 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3  50 50 — Terbuthylazine 100 55 — NO. 3 + 50 + 100 95 78 terbuthylazine

TABLE 2-57 [HYO 66] Growth inhibition rate (%) of days after treatment (4.0-5.0 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3  7 40 — Terbuthylazine 125 0 — NO. 3 + 7 + 125 98 40 terbuthylazine

TABLE 2-58 [HYO 67] Growth inhibition rate (%) of crabgrass (4.0-5.1 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3  7 80 — Aetochlor 150 0 — NO. 3 + 7 + 150 88 80 acetochlor

TABLE 2-59 [HYO 68] Growth inhibition rate (%) of velvetleaf (3.1-3.4 leaf stage) Active ingredient (20 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3  5 88 — Aetochlor 300 0 — NO. 3 + 5 + 300 90 88 acetochlor

TABLE 2-60 [HYO 69] Growth inhibition rate (%) of crabgrass (4.0-5.1 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 15 90 — S-Metolachlor 300 0 — NO. 3 + 15 + 300 99 90 S-metolachlor

TABLE 2-61 [HYO 70] Growth inhibition rate (%) of velvetleaf (3.0-3.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 15 80 — S-Metolachlor 300 0 — NO. 3 + 15 + 300 97 80 S-metolachlor

TABLE 2-62 [HYO 71] Growth inhibition rate (%) of crabgrass (4.0-5.1 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 80 — Bromoxynil- 63 0 — octanoate NO. 3 + 7 + 63 93 80 bromoxynil- octanoate

TABLE 2-63 [HYO 72] Growth inhibition rate (%) of velvetleaf (3.0-3.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 60 — Bromoxynil- 63 10 — octanoate NO. 3 + 7 + 63 100 64 bromoxynil- octanoate

TABLE 2-64 [HYO 73] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (16 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 75 — Carfentrazone 15 0 — -ethyl NO. 3 + 7 + 15 100 75 carfentrazone- ethyl

TABLE 2-65 [HYO 74] Growth inhibition rate (%) of velvetleaf (3.0-3.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 60 — Carfentrazone- 7 99 — ethyl NO. 3 + 7 + 7 100 99.6 carfentrazone- ethyl

TABLE 2-66 [HYO 75] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 80 — Pyroxasulfone 50 10 — NO. 3 + 7 + 50 95 82 pyroxasulfone

TABLE 2-67 [HYO 76] Growth inhibition rate (%) of velvetleaf (3.0-3.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 15 80 — Pyroxasulfone 50 0 — NO. 3 + 15 + 50 97 80 pyroxasulfone

TABLE 2-68 [HYO 77] Growth inhibition rate (%) of velvetleaf (3.5-4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 3.5 60 — Rimsulfuron 20 99 — NO. 3 + 3.5 + 20 100 99.6 rimsulfuron

TABLE 2-69 [HYO 78] Growth inhibition rate (%) of velvetleaf (3.0-3.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 3.5 60 — Prosulfuron 10 100 — NO. 3 + 3.5 + 10 100 100 prosulfuron

TABLE 2-70 [HYO 79] Growth inhibition rate (%) of crabgrass (5.0-5.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 3.5 65 — Alachlor 300 10 — NO. 3 + 3.5 + 300 75 69 alachlor

TABLE 2-71 [HYO 80] Growth inhibition rate (%) of velvetleaf (3.8-4.4 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 15 80 — Alachlor 300 0 — NO. 3 + 15 + 300 90 80 alachlor

TABLE 2-72 [HYO 81] Growth inhibition rate (%) of crabgrass (5.0-5.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 70 — Glyphosate- 100 10 — ammonium NO. 3 + 7 + 100 95 73 glyphosate- ammonium

TABLE 2-73 [HYO 82] Growth inhibition rate (%) of velvetleaf(3.5-4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 3.5 60 — Glyphosate- 200 15 — ammonium NO. 3 + 3.5 + 200 73 66 glyphosate- ammonium

TABLE 2-74 [HYO 83] Growth inhibition rate (%) of crabgrass (5.0-5.5 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 70 — Dicamba 200 0 — NO. 3 + 7 + 200 75 70 dicamba

TABLE 2-75 [HYO 84] Growth inhibition rate (%) of velvetleaf (3.5-4.3 leaf stage) (21 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 65 — Dicamba 100 55 — NO. 3 + 7 + 100 95 84 dicamba

TABLE 2-76 [HYO 85] Growth inhibition rate (%) of days after treatment (4.0-5.0 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 3 7 50 — Dicamba 200 0 — NO. 3 + 7 + 200 70 50 dicamba

TABLE 2-77 [HYO 86] Growth inhibition rate (%) of velvetleaf (3.8-4.4 leaf stage) (21 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 75 — Nicosulfuron 7 30 — NO. 4 + 15 + 7 97 83 nicosulfuron

TABLE 2-78 [HYO 87] Growth inhibition rate (%) of velvetleaf (3.3-3.8 leaf stage) (22 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 89 — Nicosulfuron 30 70 — 15 60 — 7 45 — 3.5 40 — NO. 4 + 15 + 30 98 97 nicosulfuron 15 + 15 99 96 15 + 7  97 94  15 + 3.5 99 93

TABLE 2-79 [HYO 88] Growth inhibition rate (%) of prickly sida Active (1.5-2.4 leaf stage) (20 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 75 55 — Nicosulfuron 15 45 — NO. 4 + 75 + 15 83 75 nicosulfuron

TABLE 2-80 [HYO 89] Growth inhibition rate (%) of crabgrass (4.0-4.5 leaf stage) (14 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 70 — Atrazine 800 40 — 400 30 — 50 20 — NO. 4 + 15 + 800 85 82 atrazine 15 + 400 83 79 15 + 50  80 76

TABLE 2-81 [HYO 90] Growth inhibition rate (%) of velvetleaf (3.1-3.5 leaf stage) (20 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 3.5 68 — Atrazine 800 100 — 600 80 — 400 40 — 200 35 00 100 30 — 50 30 NO. 4 + 3.5 + 800 100 100  atrazine 3.5 + 600 100 94 3.5 + 400 100 81 3.5 + 200 93 79 3.5 + 100 100 78 3.5 + 50  100 78

TABLE 2-82 [HYO 91] Growth inhibition rate (%) of days after treatment (4.0-5.0 leaf stage) Active ingredient (8 days after treatment) Compound amount (g/ha) Measured value Calculated value No. 4 7 65 — Atrazine 250 10 — NO. 4 + 7 + 250 95 69 atrazine

TABLE 2-83 [HYO 92] Growth inhibition rate (%) of crabgrass Active (3.5-4.3 leaf stage) (14 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 5 90 — Terbuthylazine 300 25 — NO. 4 + 5 + 300 99 93 terbuthylazine

TABLE 2-84 [HYO 93] Growth inhibition rate (%) of velvetleaf Active (3.1-3.4 leaf stage) (21 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 5 94 — Terbuthylazine 300 50 — NO. 4 + 5 + 300 100 97 terbuthylazine

TABLE 2-85 [HYO 94] Growth inhibition rate (%) of prickly Active sida (1.5-2.4 leaf stage) (20 days after ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 75 55 — Terbuthylazine 100 55 — NO. 4 + 75 + 100 93 80 terbuthylazine

TABLE 2-86 [HYO 95] Growth inhibition rate (%) of days after Active treatment (4.0-5.0 leaf stage) ingredient (8 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 7 65 — Terbuthylazine 250 10 — NO. 4 + 7 + 250 100 69 terbuthylazine

TABLE 2-87 [HYO 96] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) (14 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 7 60 — Acetochlor 150 0 — NO. 4 + 7 + 150 75 60 acetochlor

TABLE 2-88 [HYO 97] Growth inhibition rate (%) of crabgrass (3.5-5.0 leaf stage) Active ingredient (7 days after treatment) Compound amount (g/ha) Measured value Calculated value NO.4 3.5 65 — Acetochlor 750 10 — 500 0 — 250 0 — 125 0 — 63 0 — NO. 4 + 3.5 + 750 73 69 acetochlor 3.5 + 500 70 65 3.5 + 250 70 65 3.5 + 125 70 65 3.5 + 63  70 65

TABLE 2-89 [HYO 98] Growth inhibition rate (%) of velvetleaf (3.0-4.0 leaf stage) (14 days after Active ingredient treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 7 70 — Acetochlor 150 0 — NO. 4 + 7 + 150 78 70 acetochlor

TABLE 2-90 [HYO 99] Growth inhibition rate (%) of velvetleaf (2.3-3.5 leaf stage) Active ingredient (7 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 3.5 70 — Acetochlor 750 0 — 500 10 — 250 0 — 125 0 — 63 0 — NO. 4 + 3.5 + 750 73 70 acetochlor 3.5 + 250 73 70 3.5 + 63  73 70

TABLE 2-91 [HYO 100] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 7 60 — S-Metolachlor 150 0 — NO. 4 + 7 + 150 70 60 S-metolachlor

TABLE 2-92 [HYO 101] Growth inhibition rate (%) of velvetleaf (3.0-4.0 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 73 — 150  0 0 — NO. 4 + 15 + 150 83 73 S-metolachlor

TABLE 2-93 [HYO 102] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 60 — Bromoxynil- 63 0 — octanoate NO. 4 + 7 + 63 80 60 Bromoxynil- octanoate

TABLE 2-94 [HYO 103] Growth inhibition rate (%) of velvetleaf (3.2-4.1 leaf stage) Active ingredient (24 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 60 — Bromoxynil- 200 100 — octanoate NO. 4 + 7 + 200 100 100 Bromoxynil- octanoate

TABLE 2-95 [HYO 104] Growth inhibition rate (%) of Active crabgrass (4.0-5.0 leaf stage) ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 60 — Carfentrazone-ethyl 15 5 — NO. 4 + 7 + 15 70 62 carfentrazone-ethyl

TABLE 2-96 [HYO 105] Growth inhibition rate (%) of Active velvetleaf (3.0-4.0 leaf stage) ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 80 — Carfentrazone-ethyl 15 98 — NO. 4 + 15 + 15 100 99.6 carfentrazone-ethyl

TABLE 2-97 [HYO 106] Growth inhibition rate (%) of crabgrass (4.0-5.0 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 60 — Pyroxasulfone 100 5 — NO. 4 + 7 + 1-- 75 62 pyroxasulfone

TABLE 2-98 [HYO 107] Growth inhibition rate (%) of velvetleaf (3.0-4.0 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 73 — Pyroxasulfone 50 0 — NO. 4 + 15 + 50 89 73 pyroxasulfone

TABLE 2-99 [HYO 108] Growth inhibition rate (%) of crabgrass (4.0-5.1 leaf stage) Active ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 80 — Flufenacet 300 0 — NO. 4 + 7 + 300 95 80 flufenacet

TABLE 2-100 [HYO 109] Growth inhibition rate (%) of velvetleaf (3.0 to 3.5 leaf stage) Active ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  15 93 — Flufenacet 300 0 — NO. 4 + 15 + 300 98 93 flufenacet

TABLE 2-101 [HYO 110] Growth inhibition rate (%) of crabgrass (4.0-5.1 leaf stage) Active ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  15 85 — Clopyralid 300 0 — NO. 4 + 15 + 300 98 85 clopyralid

TABLE 2-102 [HYO 111] Growth inhibition rate (%) of velvetleaf (3.0-3.5 leaf stage) Active ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 75 — Clopyralid 300 35 — NO. 4 + 7 + 300 98 84 clopyralid

TABLE 2-103 [HYO 112] Growth inhibition rate (%) of Active crabgrass (4.0-5.1 leaf stage) ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  15 85 — Bentazone-sodium 200 0 — NO. 4 + 15 + 2-- 90 85 bentazone-sodium

TABLE 2-104 [HYO 113] Growth inhibition rate (%) of Active velvetleaf (3.0-3.5 leaf stage) ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 75 — Bentazone-sodium 200 30 — NO. 4 + 7 + 200 99 83 bentazone-sodium

TABLE 2-105 [HYO 114] Growth inhibition rate (%) of crabgrass (5.0-5.5 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 75 — Linuron 250 30 — NO. 4 + 7 + 250 90 83 linuron

TABLE 2-106 [HYO 115] Growth inhibition rate (%) of velvetleaf (3.2-4.1 leaf stage) Active ingredient (24 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 60 — Linuron 250 40 — NO. 4 + 7 + 250 100 76 bentazone-sodium

TABLE 2-107 [HYO 116] Growth inhibition rate (%) of crabgrass (4.0-5.1 leaf stage) Active ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 80 — Rimsulfuron 15 98 — NO. 4 + 7 + 15 100 99.6 rimsulfuron

TABLE 2-108 [HYO 117] Growth inhibition rate (%) of velvetleaf (3.0-3.5 leaf stage) Active ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 75 — Rimsulfuron 15 70 — NO. 4 + 7 + 15 99 93 rimsulfuron

TABLE 2-109 [HYO 118] Growth inhibition rate (%) of crabgrass (4.0-5.1 leaf stage) Active ingredient (23 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 85 — Prosulfuron 10 0 — NO. 4 + 15 + 10 90 85 prosulfuron

TABLE 2-110 [HYO 119] Growth inhibition rate (%) of Active crabgrass (5.0-5.5 leaf stage) ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 3.5 60 — Halofulfuron-methyl 20 0 — NO. 4 + 3.5 + 20 65 60 halosulfuron-methyl

TABLE 2-111 [HYO 120] Active Growth inhibition rate (%) of days ingredient after treatment (4.0-5.0 leaf stage) amount (21 days after treatment) Compound (g/ha) Measured value Calculated value NO. 4 7 60 — Thifensulfuron-methyl 5 0 — NO. 4 + 7 + 5 75 60 thifensulfuron-methyl

TABLE 2-112 [HYO 121] Active Growth inhibition rate (%) of giant ingredient foxtail (4.0-5.0 leaf stage) amount (14 days after treatment) Compound (g/ha) Measured value Calculated value NO. 4 7 75 — Thifensulfuron-methyl 5 0 — NO. 4 + 7 + 5 80 75 thifensulfuron-methyl

TABLE 2-113 [HYO 122] Growth inhibition rate (%) of velvetleaf (4.0-4.3 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 3.5 40 — 2,4-D ethyl 125 85 — NO. 4 + 3.5 + 125 100 91 2,4-D ethyl

TABLE 2-114 [HYO 123] Active Growth inhibition rate (%) of ingredient velvetleaf (3.2-4.1 leaf stage) amount (24 days after treatment) Compound (g/ha) Measured value Calculated value NO. 4  7 60 — Glufosinate-ammonium 200 30 — NO. 4 + 7 + 200 93 72 glufosinate-ammonium

TABLE 2-115 [HYO 124] Growth inhibition rate (%) of velvetleaf (3.2-4.1 leaf stage) Active ingredient (24 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 60 — Mesotrione 15 88 — NO. 4 + 7 + 15 99 95 mesotrione

TABLE 2-116 [HYO 125] Growth inhibition rate (%) of days after treatment (4.0-5.0 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 3.5 40 — Mesotrione 15 5 — NO. 4 + 3.5_15 50 43 mesotrione

TABLE 2-117 [HYO 126] Growth inhibition rate (%) of velvetleaf (3.2-4.1 leaf stage) Active ingredient (24 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4 15 93 — Sulcotrione 31 60 — NO. 4 + 15 + 31 99 97 sulcotrione

TABLE 2-118 [HYO 127] Growth inhibition rate (%) of days after treatment (4.0-5.0 leaf stage) Active ingredient (21 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 60 — Pyridate 100 0 — NO. 4 + 7 + 100 93 60 pyridate

TABLE 2-119 [HYO 128] Growth inhibition rate (%) of fiant foxtail (4.0-5.0 leaf stage) Active ingredient (14 days after treatment) Compound amount (g/ha) Measured value Calculated value NO. 4  7 75 — Pyridate 100 0 — NO. 4 + 7 + 100 80 75 pyridate 

The invention claimed is:
 1. A synergistic herbicidal composition, comprising, as active ingredients: a herbicidal benzoylpyrazole compound 1-(1-ethyl-4-(3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl)-1H-pyrazol-5-yloxy)ethyl methyl carbonate or its salt, and at least one other herbicidal compound selected from the group consisting of hexazinone, metribuzin, cyanazine, cybutryne, triaziflam, indaziflam, metamitron, diflufenican, bicyclopyrone, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metamifop, propaquizafop, chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, cyclosulfamuron, ethoxysulfuron, oxasulfuron, foramsulfuron, mesosulfuron-methyl, mesosulfuron, orthosulfamuron, and amidosulfuron wherein the herbicidal benzoylpyrazole compound and the at least one other herbicide compound is present in a synergistically effective amount.
 2. The synergistic herbicidal composition according to claim 1, wherein a mixing ratio of the herbicidal benzopyrazole compound or its salt to the at least one other herbicidal compound is from 1:1500 to 100:1 by weight.
 3. The synergistic herbicidal composition according to claim 2, wherein the mixing ratio is from 1:1200 to 30:1 by weight.
 4. A method for controlling undesired plants, the method comprising: applying an herbicidally effective amount of the synergistic herbicidal composition of claim 1 to an undesired plant in need thereof of or to a place where an undesired plant in need thereof grows.
 5. The method of claim 4, further comprising: applying at least one selected from the group consisting of a fungicide, an antibiotic, a plant hormone, and an insecticide to the undesired plant or to the place where the undesired plant grows.
 6. A synergistic method for controlling undesired plants, the method comprising: applying an herbicidally effective amount of 1-(1-ethyl-4-(3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl)-1H-pyrazol-5-yloxy)ethyl methyl carbonate or its salt as an herbicidal benzoylpyrazole compound and at least one other herbicidal compound to an undesired plant in need thereof or to a place where an undesired plant in need thereof grows, wherein the at least one other herbicidal compound is selected from the group consisting of hexazinone, metribuzin, cyanazine, cybutryne, triaziflam, indaziflam, metamitron, diflufenican bicyclopyrone, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metamifop, propaquizafop, chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, cyclosulfamuron, ethoxysulfuron, oxasulfuron, foramsulfuron, mesosulfuron-methyl, mesosulfuron, orthosulfamuron, and amidosulfuron wherein the herbicidal benzoylpyrazole compound and the at least one other herbicide compound is present in a synergistically effective amount.
 7. The synergistic method of claim 6, further comprising: applying at least one selected from the group consisting of a fungicide, an antibiotic, a plant hormone, and an insecticide to the undesired plant or to the place where the undesired plant grows.
 8. The synergistic herbicidal composition of claim 1, wherein the at least one other herbicidal compound is at least one compound selected from the group consisting of metribuzin, metamitron, diflufenican, bicyclopyrone, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metamifop, propaquizafop, chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, bensulfuron-methyl, bensulfuron, oxasulfuron, foramsulfuron, mesosulfuron-methyl, mesosulfuron, and orthosulfamuron.
 9. The synergistic herbicidal composition of claim 1, wherein the at least one other herbicidal compound is at least one compound selected from the group consisting of metribuzin, diflufenican, bicyclopyrone, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, metamifop-propyl, metamifop, primisulfuron-methyl, primisulfuron, and foramsulfuron. 